Tandem aldol-reduction reaction of dimethylsilyl enolates: A new method for stereoselective preparation of 1,3-diols

Authors
Miura, K Nakagawa, T Suda, S Hosomi, A
Citation
K. Miura et al., Tandem aldol-reduction reaction of dimethylsilyl enolates: A new method for stereoselective preparation of 1,3-diols, CHEM LETT, (2), 2000, pp. 150-151
Citations number
21
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
2
Year of publication
2000
Pages
150 - 151
Database
ISI
SICI code
0366-7022(20000205):2<150:TARODE>2.0.ZU;2-8
Abstract
In the presence of a catalytic amount of TBAF (Bu4NF), dimethylsilyl enolat es derived from acyclic ketones reacted with aldehydes to give syn,syn-1,3- diols 7a and 8a with moderate to high diastereoselectivity. The stereochemi cal outcome can be attributed to a syn-selective aldol reaction and the sub sequent 1,2-syn-selective intramolecular reduction.