Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: Step one in a two-step synthesis of carbohydrates

Alan B. Northrup; Ian K. Mangion; Frank Hettche; David W.C. MacMillan

doi:10.1002/anie.200453716

Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: Step one in a two-step synthesis of carbohydrates

Alan B. Northrup, Ian K. Mangion, Frank Hettche, David W.C. MacMillan

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

324 Scopus citations

Abstract

Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereo-controlled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.

Original language	English (US)
Pages (from-to)	2152-2154
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	16
DOIs	https://doi.org/10.1002/anie.200453716
State	Published - Apr 13 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Aldehydes
Aldol reaction
Carbohydrates
Enantioselectivity
Homogeneous catalysis

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10.1002/anie.200453716

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abstract = "Two-faced: α-Oxyaldehydes can act as both an aldol donor and an aldol acceptor and can be coupled enantioselectively by using proline as the reaction catalyst. This new aldol reaction provides an operationally simple protocol for the stereo-controlled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.",

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AU - Hettche, Frank

AU - MacMillan, David W.C.

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KW - Aldehydes

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KW - Carbohydrates

KW - Enantioselectivity

KW - Homogeneous catalysis

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Enantioselective organocatalytic direct aldol reactions of α-oxyaldehydes: Step one in a two-step synthesis of carbohydrates

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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