THE TETRAHYDROPYRANYL GROUP AS A CHIRAL AUXILIARY FOR THE NUCLEOPHILIC-ADDITION TO ALPHA-ALKOXY KETONES

Authors
CHARETTE AB BENSLIMANE AF MELLON C
Citation
Ab. Charette et al., THE TETRAHYDROPYRANYL GROUP AS A CHIRAL AUXILIARY FOR THE NUCLEOPHILIC-ADDITION TO ALPHA-ALKOXY KETONES, Tetrahedron letters, 36(47), 1995, pp. 8557-8560
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
8557 - 8560
Database
ISI
SICI code
0040-4039(1995)36:47<8557:TTGAAC>2.0.ZU;2-B
Abstract
The protected 2-hydroxytetrahydropyranyl group is an efficient chiral auxiliary for the stereoselective nucleophilic addition of Grignard re agents to alpha-alkoxy ketones. We also report that allylSnBu(3)MgBr(2 ) . OEt(2) is a very efficient system for the chelation controlled ste reoselective addition of the allyl group to alpha-alkoxy ketones.