Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde

Proline-Catalyzed One-Step Asymmetric Synthesis of 5-Hydroxy-(2E)-hexenal from Acetaldehyde

For the first time, the l-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the fo...

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Veröffentlicht in:Journal of organic chemistry 2002-01, Vol.67 (1), p.301-303
Hauptverfasser: Córdova, Armando, Notz, Wolfgang, Barbas, Carlos F
Format: Artikel
Sprache:eng
Schlagworte:
Acetaldehyde - chemistry
Aldehydes - chemical synthesis
Aliphatic compounds
Catalysis
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Proline - chemistry
Stereoisomerism
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Zusammenfassung:For the first time, the l-proline-catalyzed direct asymmetric self-aldolization of acetaldehyde is described affording (+)-(5S)-hydroxy-(2E)-hexenal 2 with ee's ranging from 57 to 90%. Further transformations of 2 into synthetically valuable building blocks are presented. A mechanism for the formation of 2 is proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo015881m