Dr. William A. Nugent, Ph. D.

Ph. D. with 38 years in industry and many patents and publications, currently a visiting scholar at the Ohio State University

Research Expertise

Catalysis

Biochemistry

Organic Chemistry

Drug Discovery

Physical and Theoretical Chemistry

Inorganic Chemistry

Analytical Chemistry

Pharmacology

Colloid and Surface Chemistry

Materials Chemistry

Surfaces, Coatings and Films

Ceramics and Composites

Electronic, Optical and Magnetic Materials

Metals and Alloys

Molecular Medicine

About

In my industrial career, I functioned as a toolmaker, inventing novel methodology for organic synthesis. These discoveries included the "Nugent-RajanBabu Reagent" and the "Fagan-Nugent Reaction", which are now widely used in industry and academia. I was recently thrilled to learn that I have received the 2024 Herbert C. Brown Award "for creative research in synthetic methodology" from the American Chemical Society.

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Publications

Four Mechanistic Mysteries: The Benefits of Writing a Critical Review

Angewandte Chemie

2020

Four Mechanistic Mysteries: The Benefits of Writing a Critical Review

Angewandte Chemie International Edition

2020

The reaction of β,γ−epoxy alcohols with titanium(III) reagents. A proposed role for intramolecular hydrogen bonding

Tetrahedron

2019

Demystifying Cp₂Ti(H)Cl and Its Enigmatic Role in the Reactions of Epoxides with Cp₂TiCl

Organometallics

2018

Pyrimidine as an Aryl C–H Activating Group

Organic Letters

2018

Synthesis of 4-Aryl and Unsymmetrical 4,6-Diarylpyrimidines by the Suzuki-Miyaura Cross-Coupling Reaction

HETEROCYCLES

2018

Preparation of Both C5′ Epimers of 5′-C-Methyladenosine: Reagent Control Trumps Substrate Control

The Journal of Organic Chemistry

2014

Improvement in the One‐Carbon Chain Extension of Esters with Dimethylsulfoxonium Methylide

European Journal of Organic Chemistry

2013

“Black Swan Events” in Organic Synthesis

Angewandte Chemie International Edition

2012

Selection of an Enantioselective Process for the Preparation of a CGRP Receptor Inhibitor

Organic Process Research & Development

2012

Beyond the chiral pool: a general approach to β-amino-α-keto amides

Tetrahedron

2011

Effective Oxidation of Secondary Amines to Nitrones with Alkyl Hydroperoxides Catalysed by (Trialkanolaminato)titanium(IV) Complexes

European Journal of Organic Chemistry

2010

Stereoselective Control by Face‐to‐Face Versus Edge‐to‐Face Aromatic Interactions: The Case of C₃‐Ti^IV Amino Trialkolate Sulfoxidation Catalysts

Chemistry – A European Journal

2009

2-Deoxyribose as a Rich Source of Chiral 5-Carbon Building Blocks

The Journal of Organic Chemistry

2007

Synthesis of Z-5-Carboxymethylene-1,3-dioxolan-4-ones: A Better Way

The Journal of Organic Chemistry

2007

SYNTHESIS OF AN ANTI-a-AMINO EPOXIDE BY ONE-CARBON HOMOLOGATION OF AN a-AMINO ESTER:

Organic Syntheses

2007

The Synthesis of a 5HT_2C Receptor Agonist

Organic Process Research & Development

2007

Stereoselective Process for a CCR3 Antagonist

Organic Process Research & Development

2006

Strategy for the Enantioselective Synthesis of trans-2,4-Disubstituted Piperidines: Application to the CCR3 Antagonist IS811

The Journal of Organic Chemistry

2006

(2S)-(−)-3-exo-(MORPHOLINO)ISOBORNEOL [(−)-MIB]

Organic Syntheses

2005

One-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without Diazomethane

The Journal of Organic Chemistry

2004

Ti(IV)-based catalytic membranes for efficient and selective oxidation of secondary amines

Tetrahedron Letters

2004

A ‘waterproof’ catalyst for the oxidation of secondary amines to nitrones with alkyl hydroperoxides

Tetrahedron Letters

2003

Exploring Chiral Space en route to DPC 963: A Personal Account

Advanced Synthesis & Catalysis

2003

On the Mechanism of the Oxygen Transfer to Sulfoxides by (Peroxo)[tris(hydroxyalkyl)amine]Ti^IV Complexes − Evidence for a Metal‐Template‐Assisted Process

European Journal of Organic Chemistry

2003

An Amino Alcohol Ligand for Highly Enantioselective Addition of Organozinc Reagents to Aldehydes: Serendipity Rules

Organic Letters

2002

An Efficient Large-Scale Process for the Human Leukocyte Elastase Inhibitor, DMP 777¹

Organic Process Research & Development

2001

Enantioselective Hydrogenation of 3-Alkylidenelactams: High-Throughput Screening Provides a Surprising Solution

Journal of the American Chemical Society

2002

Highly regioselective microwave-assisted synthesis of enantiopure C3-symmetric trialkanolamines

Tetrahedron Letters

2002

NMR Spectroscopic Investigations of Mixed Aggregates Underlying Highly Enantioselective 1,2-Additions of Lithium Cyclopropylacetylide to Quinazolinones

Journal of the American Chemical Society

2001

An Efficient Chiral Moderator Prepared from Inexpensive (+)-3-Carene: Synthesis of the HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitor DPC 963

Organic Letters

2000

Kinetic Investigations of Product Inhibition in the Amino Alcohol-Catalyzed Asymmetric Alkylation of Benzaldehyde with Diethylzinc

Organic Letters

2000

Enantioselective Ti(IV) Sulfoxidation Catalysts Bearing C₃-Symmetric Trialkanolamine Ligands: Solution Speciation by ¹H NMR and ESI-MS Analysis

Journal of the American Chemical Society

1999

MIB: an advantageous alternative to DAIB for the addition of organozinc reagents to aldehydes

Chemical Communications

1999

The First Chiral Zirconium(IV) Catalyst for Highly Stereoselective Sulfoxidation

The Journal of Organic Chemistry

1999

Desymmetrization of Meso Epoxides with Halides: A New Catalytic Reaction Based on Mechanistic Insight

Journal of the American Chemical Society

1998

Homogeneous catalysis as a tool for organic synthesis

Pure and Applied Chemistry

1998

Mechanistic Studies of the Zirconium−Triisopropanolamine-Catalyzed Enantioselective Addition of Azide to Cyclohexene Oxide

The Journal of Organic Chemistry

1998

Practical Synthesis of Methyl Z-2-(N-Acetylamino) but-2-Enoate. An Intermediate to D- and L-2-Aminobutyric Acid

Synthetic Communications

1998

Titanium(IV)−(R,R,R)-Tris(2-phenylethoxy)amine− Alkylperoxo Complex Mediated Oxidations: The Biphilic Nature of the Oxygen Transfer to Organic Sulfur Compounds

Journal of the American Chemical Society

1997

Use of electrospray ionization mass spectrometry to characterize chiral reactive intermediates in a titanium alkoxide mediated sulfoxidation reaction

Chemical Communications

1997

Enantioselective Titanium-Catalyzed Sulfides Oxidation: Novel Ligands Provide Significantly Improved Catalyst Life

The Journal of Organic Chemistry

1996

Highly Efficient and Enantioselective Synthesis of Carbocyclic Nucleoside Analogs Using Selective Early Transition Metal Catalysis

The Journal of Organic Chemistry

1996

Practical catalyst for cyclic metathesis. Synthesis of functional and/or enantiopure cycloalkenes.

Journal of the American Chemical Society

1995

Early Transition Metal Alkoxide Complexes Bearing Homochiral Trialkanolamine Ligands

Journal of the American Chemical Society

1994

Metallacycle Transfer from Zirconium to Main Group Elements: A Versatile Synthesis of Heterocycles

Journal of the American Chemical Society

1994

Selective Generation of Free Radicals from Epoxides Using a Transition-Metal Radical. A Powerful New Tool for Organic Synthesis

Journal of the American Chemical Society

1994

Stereoselectivity in Intramolecular Diene Cyclozirconation: A Combined Experimental and Theoretical Approach

Journal of the American Chemical Society

1994

Beyond Nature's Chiral Pool: Enantioselective Catalysis in Industry

Science

1993

Preparation and use of C2-symmetric bis(phospholanes): production of .alpha.-amino acid derivatives via highly enantioselective hydrogenation reactions

Journal of the American Chemical Society

1993

Chiral Lewis acid catalysis. Enantioselective addition of azide to meso epoxides

Journal of the American Chemical Society

1992

Free radical-mediated reduction and deoxygenation of epoxides

Journal of the American Chemical Society

1990

An unusual rotational distortion in an [(η-indenyl)RhL₂] complex: molecular structures of [(η-1,2,3-Me₃C₉H₄)Rh(η-C₂H₄)₂] and [(η-C₉H₇)Rh(CO)₂]

J. Chem. Soc., Chem. Commun.

1989

Intermolecular addition of epoxides to activated olefins: a new reaction

Journal of the American Chemical Society

1989

Lewis acid effects on selectivity in nickel-catalyzed pentenenitrile hydrocyanation. Triorganotin salts as tunable Lewis acid promoters

Organometallics

1989

Zirconium-mediated ring construction from dienes: remarkable effect of ligands on stereochemistry

Journal of the American Chemical Society

1989

Copper (II) Supported on Nafion® Perfluorinated Ion Exchange Polymer: An Efficient Catalyst For Cyclopropanation Reactions

Synthetic Communications

1988

Stereoselective cyclization of enynes mediated by metallocene reagents

Journal of the American Chemical Society

1988

Synthesis of main group heterocycles by metallacycle transfer from zirconium

Journal of the American Chemical Society

1988

Transition-metal-centered radicals in organic synthesis. Titanium(III)-induced cyclization of epoxy olefins

Journal of the American Chemical Society

1988

A general method for the preparation of zirconocene complexes of substituted benzynes: in situ generation, coupling reactions, and use in the synthesis of polyfunctionalized aromatic compounds

Journal of the American Chemical Society

1987

Cyclization of diacetylenes to E,E exocyclic dienes. Complementary procedures based on titanium and zirconium reagents

Journal of the American Chemical Society

1987

Catalytic hydrogen-deuterium exchange in deuteriated alcohols promoted by early-transition-metal alkoxides. Insight into a mechanistic puzzle

Inorganic Chemistry

1986

Improved route to 3-vinyl substituted cyclopentanones. Synthesis of (.+-.)-mitsugashiwalactone

The Journal of Organic Chemistry

1986

A new role for organometallic reactions in organic synthesis in industry

Pure and Applied Chemistry

1985

Homogeneous models for propylene ammoxidation. 2. The carbon-nitrogen bond-forming step

Inorganic Chemistry

1985

Homogeneous models for propylene ammoxidation. 1. Tungsten(VI) imido complexes as models for the active sites

Journal of the American Chemical Society

1985

Linear dimerization of acrylates by palladium and rhodium catalysts: effect of lewis and protic acid additives

Journal of Molecular Catalysis

1985

Nickel-catalyzed Markovnikov addition of hydrogen cyanide to olefins. Application to nonsteroidal antiinflammatories

The Journal of Organic Chemistry

1985

Selective C-C bond formation by the photolysis of unsymmetrical organomercurials

Inorganica Chimica Acta

1984

Solvated triorganotin cations. Structure and use as catalysts for Diels-Alder additions to furan

Organometallics

1984

Titanium-mediated synthesis of (E,E)-exocyclic dienes. Application to the preparation of polycyclic compounds

Journal of the American Chemical Society

1984

A regiospecific, convergent route to 2,3-disubstituted cyclopentanones

The Journal of Organic Chemistry

1983

Catalytic C-H activation in early transition-metal dialkylamides and alkoxides

Organometallics

1983

Reaction of allyltin reagents with perfluoroalkyl nitriles

Journal of Organometallic Chemistry

1983

Synthesis of some d0 organoimido complexes of the early transition metals

Inorganic Chemistry

1983

Electrophilic vs. nucleophilic reactivity in complexes containing multiply-bonded (alkylidene, imido or oxo) ligands. A conceptual model

Inorganica Chimica Acta

1982

Iron catalysis of grignard reductions. Mechanism of 1, 3-reductive eliminations from γ-propyl halides

Journal of Organometallic Chemistry

1982

Structures of [(CH3)2(t-BuN)W]2(.mu.-t-BuN)2 and [((CH3)2N)2Ti]2(.mu.-t-BuN)2. A molecular orbital explanation of the existence of unsymmetrically or symmetrically bridging organoimido ligands

Journal of the American Chemical Society

1981

Molecular distortions in sterically congested organometals. Crystal structure of bis(2,4,6-tri-tert-butylphenyl)mercury

Inorganic Chemistry

1980

Reaction of Group VIB organoimido complexes with organozinc. Reductive elimination across a metal-nitrogen multiple bond

Journal of the American Chemical Society

1980

Some bis(tert-butylimido) complexes of the Group 6 transition metals and a related alkylamido derivative

Inorganic Chemistry

1980

Transition metal complexes containing organoimido (nr) and related ligands

Coordination Chemistry Reviews

1980

Unusual reactions of adamantylideneadamantane with metal oxidants. Isolation of stable chloronium salts

The Journal of Organic Chemistry

1980

Bridging alkylimido complexes of the Group 4B transition metals

Inorganic Chemistry

1979

Intramolecular comparison of the .pi.-donor capability of oxo and organoimido ligands. X-ray crystal structures of N-1-adamantylimidotrioxoosmium and bis(N-tert-butylimido)dioxoosmium

Journal of the American Chemical Society

1979

Stable first-row transition metal alkylimido complexes; X-ray crystal and molecular structure of N-(1-adamantylimido)tris(trimethylsiloxy)vanadium(V)

Journal of the Chemical Society, Chemical Communications

1979

The first d⁰organoimido complexes of rhenium. X-Ray crystal and molecular structure of µ-oxo-µ-trimethylsilyloxo-µ-perrhenato-bis-(di-t-butylimidotrimethylsilyloxorhenium)

J. Chem. Soc., Chem. Commun.

1979

-generated molybdenum (VI) reagent for -chlorination of alkenes

Tetrahedron Letters

1978

Structure and reactivity in the group 5Bt-butylimido complexes (Me₂N)₃MNBu^t; X-ray crystal and molecular structure of N-t-butylimidotris(dimethylamido)tantalum

J. Chem. Soc., Chem. Commun.

1978

Organomercurials I. Free radical chain mechanisms in the reductive elimination of dialkylmercury in carbon tetrachloride

Journal of Organometallic Chemistry

1977

Organomercurials. II. Substitution processes in the homolytic cleavage of dialkylmercury the formation of alkylmercury(II) derivatives

Journal of Organometallic Chemistry

1977

Organomercurials. III. Initiation processes in the homolytic cleavage of dialkylmercury. Spontaneous reaction of di-tert-butylmercury in carbon tetrachloride

Journal of Organometallic Chemistry

1977

Alkyl substituent effects in electrophilic substitution at saturated carbon. Inapplicability of Taft .sigma.* values

Journal of the American Chemical Society

1976

Effect of alkyl substituents on the first ionization potential and on 5d10 ionization in dialkylmercury compounds

Inorganic Chemistry

1976

Electrophilic substitution at saturated carbon in mercurials. Alkyl ligands as mechanistic probes in the cleavage of organometals

Journal of the American Chemical Society

1976

Enhanced reactivity of exo-norbornyl derivatives. Evidence for σ-participation in the absence of steric effects

J. Chem. Soc., Chem. Commun.

1976

Reductive elimination of organometals by free radical chain mechanisms. Enhanced activation of .beta.-hydrogens in dialkylmercury

Journal of the American Chemical Society

1976

Electron transfer from organolithium and Grignard reagents. Reactions with peroxides

Journal of the American Chemical Society

1974

Education

Indiana University Bloomington

Ph. D. in Organic Chemistry, Chemistry / November, 1976

Bloomington, Indiana, United States of America

Purdue University West Lafayette

B. S., Chemistry / June, 1969

West Lafayette

Indiana University Bloomington

Ph. D. in Organic Chemistry, Chemistry / November, 1976

Bloomington, Indiana, United States of America

Purdue University West Lafayette

B. S., Chemistry / June, 1969

West Lafayette

Experience

The Ohio State University

Visiting Scholar / June, 2015 — Present

Vertex Pharmaceuticals

Senior Scientific Fellow / July, 2007 — 2014

Bristol-Myers Squibb

Senior Research Fellow / 2001 — July, 2007

DuPont Pharmaceutical Company

Research Fellow / April, 1999 — 2001

DuPont

Research Chemist / November, 1976 — April, 1999

Archbishop Alter High School

Chemistry and Physics Teacher / August, 1969 — June, 1972

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