THE 2-BENZYLOXYTETRAHYDROPYRANYL GROUP AS A CHIRAL AUXILIARY FOR THE NUCLEOPHILIC-ADDITION TO ALPHA-ALKOXY ALDEHYDES

Authors
CHARETTE AB MELLON C MOTAMEDI M
Citation
Ab. Charette et al., THE 2-BENZYLOXYTETRAHYDROPYRANYL GROUP AS A CHIRAL AUXILIARY FOR THE NUCLEOPHILIC-ADDITION TO ALPHA-ALKOXY ALDEHYDES, Tetrahedron letters, 36(47), 1995, pp. 8561-8564
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
47
Year of publication
1995
Pages
8561 - 8564
Database
ISI
SICI code
0040-4039(1995)36:47<8561:T2GAAC>2.0.ZU;2-L
Abstract
The addition of Grignard reagents, hydride reagents and crotylstannane s to an alpha-alkoxy carbonyl bearing the 2-benzyloxytetrahydropyranyl group showed good levels of diastereofacial control. The sense of ind uction was the same as that reported for the addition of allylSnBu(3). An important solvent effect consistent with the proposed transition s tate model was observed in these reactions.