ASYMMETRIC CARBONYL ADDITION-REACTIONS TO BENZYLOXYALDEHYDES BY BINAPHTHOL-TITANIUM CATALYST ANTI-DIASTEREOFACIAL VS SYN-DIASTEREOFACIAL PREFERENCE IN ANOMALOUS NONCHELATION COMPLEXATION

Authors
MIKAMI K MATSUKAWA S SAWA E HARADA A KOGA N
Citation
K. Mikami et al., ASYMMETRIC CARBONYL ADDITION-REACTIONS TO BENZYLOXYALDEHYDES BY BINAPHTHOL-TITANIUM CATALYST ANTI-DIASTEREOFACIAL VS SYN-DIASTEREOFACIAL PREFERENCE IN ANOMALOUS NONCHELATION COMPLEXATION, Tetrahedron letters, 38(11), 1997, pp. 1951-1954
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
11
Year of publication
1997
Pages
1951 - 1954
Database
ISI
SICI code
0040-4039(1997)38:11<1951:ACATBB>2.0.ZU;2-V
Abstract
An anomalous nonchelation diastereofacial selectivity is observed in t he titanium-catalyzed carbonyl addition reaction to benzyl-protected a lkoxyaldehydes. There is a dichotomy in the sense of syn- vs. anti-dia stereofacial preference, dictated by the bulkiness of the migratory gr oup: The sterically demanding silyl group gives syn-diastereofacial pr eference and the less sterically demanding proton lends to anti-diaste reofacial preference. (C) 1997 Elsevier Science Ltd.