DIASTEREOSELECTIVE REACTIONS OF GRIGNARD-REAGENTS WITH CHIRAL AMINO LACTOLS DERIVED FROM L-ASPARTIC ACID

Authors
YODA H NAKAGAMI Y TAKABE K
Citation
H. Yoda et al., DIASTEREOSELECTIVE REACTIONS OF GRIGNARD-REAGENTS WITH CHIRAL AMINO LACTOLS DERIVED FROM L-ASPARTIC ACID, Tetrahedron : asymmetry, 5(2), 1994, pp. 169-172
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
2
Year of publication
1994
Pages
169 - 172
Database
ISI
SICI code
0957-4166(1994)5:2<169:DROGWC>2.0.ZU;2-Q
Abstract
Nucleophilic additions to chiral amino lactols obtained from L-asparti c acid containing a chiral alpha-silyloxymethyl function by simple Gri gnard reagents exhibited high stereoselectivity to provide the corresp onding optically active amino alcohols containing three contiguous ste reogenic centers. The mechanistic origin of the asymmetric induction i s rationalized based on chelation controlled models.