Organocatalytic and Enantioselective Synthesis of β-(Hydroxyalkyl)-γ-Butyrolactones

Organocatalytic cross-aldol reaction of methyl 4-oxobutyrate (2) and a variety of aldehydes 3 followed by reduction with NaBH4 has provided a one-pot, general and efficient method for the synthesis of 4-(hydroxyalkyl)-γ-butyrolactones 1 with high diastereo- (dr > 24:1) and enantioselectivity (ee...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-05, Vol.73 (10), p.3935-3937
Main Authors: Hajra, Saumen, Giri, Aswini Kumar
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Catalysis
Chemistry
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Models, Molecular
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:Organocatalytic cross-aldol reaction of methyl 4-oxobutyrate (2) and a variety of aldehydes 3 followed by reduction with NaBH4 has provided a one-pot, general and efficient method for the synthesis of 4-(hydroxyalkyl)-γ-butyrolactones 1 with high diastereo- (dr > 24:1) and enantioselectivity (ee > 99%).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo8005733