DIASTEREOCONTROL IN LEWIS ACID-CATALYZED MICHAEL REACTIONS OF 4-SILOXYCYCLOPENTENONE WITH KETENE SILYL ACETALS - STEREOELECTRONIC VS STERICEFFECT

Authors
OTERA J FUJITA Y FUKUZUMI S HIRAI K GU JH NAKAI T
Citation
J. Otera et al., DIASTEREOCONTROL IN LEWIS ACID-CATALYZED MICHAEL REACTIONS OF 4-SILOXYCYCLOPENTENONE WITH KETENE SILYL ACETALS - STEREOELECTRONIC VS STERICEFFECT, Tetrahedron letters, 36(1), 1995, pp. 95-98
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
1
Year of publication
1995
Pages
95 - 98
Database
ISI
SICI code
0040-4039(1995)36:1<95:DILAMR>2.0.ZU;2-T
Abstract
The title reactions are shown to proceed with sterically unfavorable s yn preference (to the siloxy group) when steric demand of the acetals is trivial, whereas beta-substitution of acetals results in reversal o f diastereoselection. These results are discussed in terms of the ster eoelectronic vs. steric effect.