Thieme Chemistry Journal awardees - Where are they now? Intermolecular cross-acyloin reactions by fluoride-promoted additions of O-silyl thiazolium carbinols

Alex K. Mathies; Anita E. Mattson; Karl A. Scheidt

doi:10.1055/s-0028-1087555

Thieme Chemistry Journal awardees - Where are they now? Intermolecular cross-acyloin reactions by fluoride-promoted additions of O-silyl thiazolium carbinols

Alex K. Mathies, Anita E. Mattson, Karl A. Scheidt

Chemistry

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

The addition of acyl anion equivalents to aliphatic aldehydes (crossed-acyloin reaction) has been developed. Cesium fluoride with isopropanol as solvent promotes the addition of O-silyl thiazolium carbinols to various aliphatic aldehydes in moderate to good yields. These reactions represent a general procedure for the selective coupling of aliphatic aldehydes by an acyl anion reaction which have been problematic until now.

Original language	English (US)
Pages (from-to)	377-383
Number of pages	7
Journal	Synlett
Issue number	3
DOIs	https://doi.org/10.1055/s-0028-1087555
State	Published - Feb 2009

Keywords

Acyl anions
Acyloin reaction
Carbinols
Cesium fluoride
Thiazolium

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The addition of acyl anion equivalents to aliphatic aldehydes (crossed-acyloin reaction) has been developed. Cesium fluoride with isopropanol as solvent promotes the addition of O-silyl thiazolium carbinols to various aliphatic aldehydes in moderate to good yields. These reactions represent a general procedure for the selective coupling of aliphatic aldehydes by an acyl anion reaction which have been problematic until now.",

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language = "English (US)",

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AU - Scheidt, Karl A.

PY - 2009/2

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N2 - The addition of acyl anion equivalents to aliphatic aldehydes (crossed-acyloin reaction) has been developed. Cesium fluoride with isopropanol as solvent promotes the addition of O-silyl thiazolium carbinols to various aliphatic aldehydes in moderate to good yields. These reactions represent a general procedure for the selective coupling of aliphatic aldehydes by an acyl anion reaction which have been problematic until now.

AB - The addition of acyl anion equivalents to aliphatic aldehydes (crossed-acyloin reaction) has been developed. Cesium fluoride with isopropanol as solvent promotes the addition of O-silyl thiazolium carbinols to various aliphatic aldehydes in moderate to good yields. These reactions represent a general procedure for the selective coupling of aliphatic aldehydes by an acyl anion reaction which have been problematic until now.

KW - Acyl anions

KW - Acyloin reaction

KW - Carbinols

KW - Cesium fluoride

KW - Thiazolium

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Thieme Chemistry Journal awardees - Where are they now? Intermolecular cross-acyloin reactions by fluoride-promoted additions of O-silyl thiazolium carbinols

Abstract

Keywords

ASJC Scopus subject areas

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