Diastereoselectivity in the addition and cycloaddition reactions of a chiral ester of 2H-azirine-3-carboxylic acid

Authors
Alves, MJ Bickley, JF Gilchrist, TL
Citation
Mj. Alves et al., Diastereoselectivity in the addition and cycloaddition reactions of a chiral ester of 2H-azirine-3-carboxylic acid, J CHEM S P1, (11), 1999, pp. 1399-1401
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
11
Year of publication
1999
Pages
1399 - 1401
Database
ISI
SICI code
0300-922X(19990607):11<1399:DITAAC>2.0.ZU;2-Z
Abstract
The azirine ester 2 bearing Oppolzer's N,N-diethyl-(1R)isobornyl-10-sulfona mide chiral auxiliary shows moderate diastereoselectivity in its Diels-Alde r reaction with cyclopentadiene whereas the addition of thiophenol is highl y diastereoselective; X-ray crystal structures of the aziridine esters 6 an d 7 are reported.