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Enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes. Chiral building blocks for 2-pyrrolidinones and other derivatives.

Authors
Type
Published Article
Journal
Organic Letters
1523-7052
Publisher
American Chemical Society
Publication Date
Volume
12
Issue
13
Pages
3058–3061
Identifiers
DOI: 10.1021/ol1010888
PMID: 20536220
Source
Medline
License
Unknown

Abstract

A catalytic highly enantioselective Henry addition of methyl 4-nitrobutyrate to aldehydes using a Cu(II)-amino pyridine complex as catalyst is described. The products resulting from this reaction constitute a new, highly versatile family of chiral building blocks as a result of the presence of three different functional groups on the molecule. These products have been transformed into nonracemic chiral gamma-lactams, 5-hydroxy-5-substituted levulinic acid derivatives, and delta-lactones.

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