ASYMMETRIC BAYLLIS-HILLMAN REACTIONS USING CHIRAL 2,3-DISUBSTITUTED 1,4-DIAZABICYCLO[2.2.2]OCTANES CATALYSTS UNDER HIGH-PRESSURE CONDITIONS

Authors
OISHI T OGURI H HIRAMA M
Citation
T. Oishi et al., ASYMMETRIC BAYLLIS-HILLMAN REACTIONS USING CHIRAL 2,3-DISUBSTITUTED 1,4-DIAZABICYCLO[2.2.2]OCTANES CATALYSTS UNDER HIGH-PRESSURE CONDITIONS, Tetrahedron : asymmetry, 6(6), 1995, pp. 1241-1244
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
6
Year of publication
1995
Pages
1241 - 1244
Database
ISI
SICI code
0957-4166(1995)6:6<1241:ABRUC2>2.0.ZU;2-K
Abstract
Chiral C-2-symmetric 2,3-disubstituted 1,4-diazabicyclo[2,2.2]octanes (DABCOs) (1) have been utilized as catalysts for asymmetric Baylis-Hil lman reactions. Optically active alpha-methylene-beta-hydroxyalkanone was obtained in up to 47% ee. Under high pressure conditions, a remark able enhancement of both reaction rate and enantioselectivity has been observed.