Diastereoselective additions of nucleophiles to hindered alpha-trimethylsilyloxy aldehydes

Citation
D. Bourgeois et al., Diastereoselective additions of nucleophiles to hindered alpha-trimethylsilyloxy aldehydes, SYNLETT, (3), 2000, pp. 323-326
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
3
Year of publication
2000
Pages
323 - 326
Database
ISI
SICI code
0936-5214(200003):3<323:DAONTH>2.0.ZU;2-A
Abstract
High diastereoselectivity was observed for the additions of hindered nucleo philes such as 6c to hindered alpha-trimethylsilyloxyaldehydes 5 and 10, le ading to trans-diols. Concomitant silyl tranfer to the incipient secondary alcohol could explain this unusual selectivity.