Highly diastereoselective Michael addition of alpha-hydroxy acid derivatives and enantioselective synthesis of (+)-crobarbatic acid

Authors
Jang, DP Chang, JW Uang, BJ
Citation
Dp. Jang et al., Highly diastereoselective Michael addition of alpha-hydroxy acid derivatives and enantioselective synthesis of (+)-crobarbatic acid, ORG LETT, 3(7), 2001, pp. 983-985
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
7
Year of publication
2001
Pages
983 - 985
Database
ISI
SICI code
1523-7060(20010405)3:7<983:HDMAOA>2.0.ZU;2-Z
Abstract
Michael addition of enolates of 2a and 2b to alpha, beta -unsaturated ester s took place selectively on different faces (Si and Re, respectively) of th e double bond to give the corresponding products 4 and 5, respectively, wit h >98% de. Subsequent hydrolysis of these Micheal adducts gives 3,4-disubst ituted gamma -lactones with high enantiomeric excesses.