期刊
TETRAHEDRON
卷 68, 期 10, 页码 2326-2335出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.01.039
关键词
Asymmetric thia-hetero-Diels-Alder reaction; Chiral dithioester; Bis(oxazoline); Cu(II) catalyst; Double-stereodifferentiating experiments; Theoretical study
资金
- Ministere de la Recherche et des Nouvelles Technologies
- 'CRUNCHOrga' (Centre de Recherche Universitaire Normand de Chimie Organique)
- Region Basse-Normandie
- Centre National de la Recherche Scientifique (CNRS)
- European Union
Asymmetric thia-Diels-Alder reactions involving new dithioesters bearing a chiral auxiliary are described, with diastereoselectivities up to 78%. Double-stereodifferentiating experiments employing chiral substrates in the presence of a chiral Lewis acid catalyst have been also carried out and, in this case, a diastereomeric excess of 90% was reached. The absolute stereochemistry of cycloadducts resulting from dithiooxalates and carbonyloxazolidinone dithioesters was assigned based on an X-ray structure and chemical correlation. In order to rationalize the sense of the chiral induction, stereochemical models for Cu(II)/bis(oxazoline)/dithioester complexes are proposed. (C) 2012 Elsevier Ltd. All rights reserved.
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