AN EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE AXIALLY CHIRAL ANILIDE ANDITS APPLICATION TO IODINE-MEDIATED ASYMMETRIC DIELS-ALDER REACTION

Authors
KITAGAWA O IZAWA H TAGUCHI T SHIRO M
Citation
O. Kitagawa et al., AN EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE AXIALLY CHIRAL ANILIDE ANDITS APPLICATION TO IODINE-MEDIATED ASYMMETRIC DIELS-ALDER REACTION, Tetrahedron letters, 38(25), 1997, pp. 4447-4450
Citations number
5
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
25
Year of publication
1997
Pages
4447 - 4450
Database
ISI
SICI code
0040-4039(1997)38:25<4447:AESOOA>2.0.ZU;2-T
Abstract
A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high opt ical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl l actic acid and N-allyl o-t-butylaniline. Iodine-mediated Diels-Alder r eaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity. (C) 1997 Elsevier S cience Ltd.