LEWIS ACID-MEDIATED REACTION WITH SILYL KETENE ACETALS AND ALLYLSTANNANE OF THE ALUMINUM ACETALS GENERATED BY DIBALH REDUCTION OF ALPHA-AMINO-ACID ESTERS

Authors
KIYOOKA S SUZUKI K SHIROUCHI M KANEKO Y TANIMORI S
Citation
S. Kiyooka et al., LEWIS ACID-MEDIATED REACTION WITH SILYL KETENE ACETALS AND ALLYLSTANNANE OF THE ALUMINUM ACETALS GENERATED BY DIBALH REDUCTION OF ALPHA-AMINO-ACID ESTERS, Tetrahedron letters, 34(36), 1993, pp. 5729-5732
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
36
Year of publication
1993
Pages
5729 - 5732
Database
ISI
SICI code
0040-4039(1993)34:36<5729:LARWSK>2.0.ZU;2-K
Abstract
The intermediates generated by DIBALH reduction of alpha-amino acid es ters undergo condensation without racemization with silyl ketene aceta ls and allylstannane in the presence of Lewis acid to afford the corre sponding beta-hydroxy esters and homoallylic alcohols in good yields w hile achieving high syn selectivity via an aluminum-assisted chelation control.