Acyloin Coupling Reactions

K. A. Scheidt; E. A. O'Bryan

doi:10.1016/B978-0-08-097742-3.00317-7

Acyloin Coupling Reactions

K. A. Scheidt^*, E. A. O'Bryan

^*Corresponding author for this work

Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Chapter

14 Scopus citations

Abstract

The α-hydroxy ketone group, or acyloin, is prevalent in natural products and pharmaceuticals, and the development of efficient methods to install this functional group remains an important synthetic challenge. As a result, several distinct methods for the synthesis of α-hydroxy ketones have been developed. This chapter presents a review of approaches toward this structural motif in which the acyloin is derived from the coupling of two carbonyl units to form a new carbon-carbon σ-bond. This definition encompasses the traditional acyloin condensation, involving the reductive coupling of two aliphatic esters, and recent catalytic approaches that invoke acyl anion intermediates (umpolung reactivity).

Original language	English (US)
Title of host publication	Comprehensive Organic Synthesis
Subtitle of host publication	Second Edition
Publisher	Elsevier Ltd
Pages	621-655
Number of pages	35
Volume	3
ISBN (Print)	9780080977430
DOIs	https://doi.org/10.1016/B978-0-08-097742-3.00317-7
State	Published - Feb 2014

Keywords

Acyl anion equivalent
Acyloin
Benzoin
N-heterocyclic carbene
Organocatalysis
Reductive coupling
Umpolung
α-Hydroxy ketone

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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10.1016/B978-0-08-097742-3.00317-7

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title = "Acyloin Coupling Reactions",

abstract = "The α-hydroxy ketone group, or acyloin, is prevalent in natural products and pharmaceuticals, and the development of efficient methods to install this functional group remains an important synthetic challenge. As a result, several distinct methods for the synthesis of α-hydroxy ketones have been developed. This chapter presents a review of approaches toward this structural motif in which the acyloin is derived from the coupling of two carbonyl units to form a new carbon-carbon σ-bond. This definition encompasses the traditional acyloin condensation, involving the reductive coupling of two aliphatic esters, and recent catalytic approaches that invoke acyl anion intermediates (umpolung reactivity).",

keywords = "Acyl anion equivalent, Acyloin, Benzoin, N-heterocyclic carbene, Organocatalysis, Reductive coupling, Umpolung, α-Hydroxy ketone",

author = "Scheidt, {K. A.} and O'Bryan, {E. A.}",

note = "Funding Information: Karl A. Scheidt is currently the Alumnae of Northwestern Teaching Professor, an Alfred P. Sloan fellow, an ACS Research Scholar, and past recipient of an NSF CAREER Award. He received his undergraduate degree from Notre Dame in 1994 while working in the laboratory of Professor Marvin J. Miller. Under the direction of Prof. William R. Roush, he earned his PhD from Indiana University and was a National Institutes of Health Postdoctoral Fellow in the laboratory of Prof. David Evans at Harvard University. Ongoing research interests include developing new organosilicon methodology and catalytic processes involving NHCs. Using carbene catalysis, his research group has developed numerous innovative approaches to carbonyl/acyl anion equivalents, homoenolate reactivity, hydroacylations of ketones, formal [2+3] and [3+3] cycloadditions, Michael reactions, and acylvinyl anion equivalents. The Scheidt laboratory is also engaged in the synthesis and chemical biology of natural products with antitumor activity. ",

year = "2014",

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doi = "10.1016/B978-0-08-097742-3.00317-7",

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PY - 2014/2

Y1 - 2014/2

N2 - The α-hydroxy ketone group, or acyloin, is prevalent in natural products and pharmaceuticals, and the development of efficient methods to install this functional group remains an important synthetic challenge. As a result, several distinct methods for the synthesis of α-hydroxy ketones have been developed. This chapter presents a review of approaches toward this structural motif in which the acyloin is derived from the coupling of two carbonyl units to form a new carbon-carbon σ-bond. This definition encompasses the traditional acyloin condensation, involving the reductive coupling of two aliphatic esters, and recent catalytic approaches that invoke acyl anion intermediates (umpolung reactivity).

AB - The α-hydroxy ketone group, or acyloin, is prevalent in natural products and pharmaceuticals, and the development of efficient methods to install this functional group remains an important synthetic challenge. As a result, several distinct methods for the synthesis of α-hydroxy ketones have been developed. This chapter presents a review of approaches toward this structural motif in which the acyloin is derived from the coupling of two carbonyl units to form a new carbon-carbon σ-bond. This definition encompasses the traditional acyloin condensation, involving the reductive coupling of two aliphatic esters, and recent catalytic approaches that invoke acyl anion intermediates (umpolung reactivity).

KW - Acyl anion equivalent

KW - Acyloin

KW - Benzoin

KW - N-heterocyclic carbene

KW - Organocatalysis

KW - Reductive coupling

KW - Umpolung

KW - α-Hydroxy ketone

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BT - Comprehensive Organic Synthesis

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Acyloin Coupling Reactions

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