ASYMMETRIC DESYMMETRIZATION OF PROCHIRAL 1,3-DIOLS VIA DIASTEREOSELECTIVE C-O BOND FISSION OF BICYCLIC ACETAL USING A CHIRAL SULFOXIDE AS ACHIRAL AUXILIARY

Authors
MAEZAKI N MURAKAMI M SOEJIMA M TANAKA T IWANISHI T IWATA C
Citation
N. Maezaki et al., ASYMMETRIC DESYMMETRIZATION OF PROCHIRAL 1,3-DIOLS VIA DIASTEREOSELECTIVE C-O BOND FISSION OF BICYCLIC ACETAL USING A CHIRAL SULFOXIDE AS ACHIRAL AUXILIARY, Chemical and Pharmaceutical Bulletin, 44(6), 1996, pp. 1146-1151
Citations number
42
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
44
Issue
6
Year of publication
1996
Pages
1146 - 1151
Database
ISI
SICI code
0009-2363(1996)44:6<1146:ADOP1V>2.0.ZU;2-I
Abstract
Asymmetric desymmetrization of a prochiral 1,3-diol was established by diastereoselective C-O bond fission of the chiral alpha-sulfinyl acet al 6, Treatment of 6 with titanium tetrachloride afforded mainly 7a vi a an oxonium intermediate, while with lithium diisopropylamide 7b was selectively obtained, in diastereoselective beta-elimination followed by an olefin isomerization.