METAL VERSUS SILYL TRIFLATE CATALYSIS IN THE MUKAIYAMA ALDOL ADDITION-REACTION

Authors
CARREIRA EM SINGER RA
Citation
Em. Carreira et Ra. Singer, METAL VERSUS SILYL TRIFLATE CATALYSIS IN THE MUKAIYAMA ALDOL ADDITION-REACTION, Tetrahedron letters, 35(25), 1994, pp. 4323-4326
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
25
Year of publication
1994
Pages
4323 - 4326
Database
ISI
SICI code
0040-4039(1994)35:25<4323:MVSTCI>2.0.ZU;2-#
Abstract
A mechanistic study of the Mukaiyama aldol addition reaction employing benzaldehyde and hydrocinnamaldehyde along with a selection of Lewis acids including BF3.OEt(2), LiClO4, Yb(OTf)(3), Sn(OTf)(2), and Zn(OTf )(2) is presented. The results of experiments conducted with doubly-la beled silyl ketene acetals implicate a Lewis acidic silicon species an d not the metals as the catalyst in the Mukaiyama aldol addition react ion.