AN EFFICIENT ASYMMETRIC ALDOL REACTION OF 4-TRIMETHYLSILOXY-6-METHYLENE-1,3-DIOXINES BY CHIRAL BINAPHTHOL-TITANIUM COMPLEX CATALYSIS

Authors
SATO M SUNAMI S SUGITA Y KANEKO C
Citation
M. Sato et al., AN EFFICIENT ASYMMETRIC ALDOL REACTION OF 4-TRIMETHYLSILOXY-6-METHYLENE-1,3-DIOXINES BY CHIRAL BINAPHTHOL-TITANIUM COMPLEX CATALYSIS, Heterocycles, 41(7), 1995, pp. 1435-1444
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
41
Issue
7
Year of publication
1995
Pages
1435 - 1444
Database
ISI
SICI code
0385-5414(1995)41:7<1435:AEAARO>2.0.ZU;2-D
Abstract
The asymmetric aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dio xines or the 6-ethylidene analogue with achiral aldehydes proceeds in a highly enantioselective manner under chiral binaphthol-titanium comp lex catalysis to afford 6-substituted 1,3-dioxin-4-ones which serve as chemical equivalents of delta-hydroxy-beta-keto esters, potential chi ral building blocks. An explanation for the stereoselectivity is also presented.