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Enantioselective Organocatalytic Direct Aldol Reactions of α‐Oxyaldehydes: Step One in a Two‐Step Synthesis of Carbohydrates

Year: 2004

Type: article

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 stereocontrolled production of erythrose (see scheme) architecture and sets the stage for a two-step enantioselective synthesis of carbohydrates.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.200453716

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

Institution: California Institute of Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

OpenAlex ID: W2169392145

FWCI: 23.36

Cites: 27

Cited by: 320

Related to: 10