1,6-ASYMMETRIC INDUCTION BY REDUCTIVE ACETAL CLEAVAGE OF A BICYCLIC ACETAL USING A SULFINYL CHIRAL AUXILIARY

Authors
MAEZAKI N SHOGAKI T IMAMURA T TOKUNO K OHKUBO K TANAKA T IWATA C
Citation
N. Maezaki et al., 1,6-ASYMMETRIC INDUCTION BY REDUCTIVE ACETAL CLEAVAGE OF A BICYCLIC ACETAL USING A SULFINYL CHIRAL AUXILIARY, Chemical and Pharmaceutical Bulletin, 46(5), 1998, pp. 837-841
Citations number
14
Categorie Soggetti
Chemistry Medicinal",Chemistry,"Pharmacology & Pharmacy
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
46
Issue
5
Year of publication
1998
Pages
837 - 841
Database
ISI
SICI code
0009-2363(1998)46:5<837:1IBRAC>2.0.ZU;2-3
Abstract
A new synthetic route to a chiral 2,5-disubstituted tetrahydropyran ha s been achieved by asymmetric reductive acetal cleavage of a bicyclic acetal having a chiral sulfinyl group as a chiral auxiliary. It was fo und that the (5S)-tetrahydropyran was obtained preferentially (up to 9 6:4) with an R-sulfinyl chiral auxiliary by an efficient 1,6-asymmetri c induction from sulfinyl chirality to the prochiral center on the bic yclic ring.