Asymmetric synthesis of gamma-hydroxy alpha,beta-unsaturated aldehydes viaenantioselective direct addition of propargyl acetate to aldehydes

Authors
El-Sayed, E Anand, NK Carreira, EM
Citation
E. El-sayed et al., Asymmetric synthesis of gamma-hydroxy alpha,beta-unsaturated aldehydes viaenantioselective direct addition of propargyl acetate to aldehydes, ORG LETT, 3(19), 2001, pp. 3017-3020
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
19
Year of publication
2001
Pages
3017 - 3020
Database
ISI
SICI code
1523-7060(20010920)3:19<3017:ASOGAA>2.0.ZU;2-G
Abstract
[GRAPHICS] We report the first example of enantioselective and diastereoselective alde hyde additions of propargyl acetate to aldehydes using the methodology rece ntly reported from our laboratories. Subsequent O-silyl protection, Pd-cata lyzed isomerization, AcOH addition, and hydrolysis result in optically acti ve gamma -hydroxy alpha,beta -unsaturated aldehydes as powerful building bl ocks.