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Enantioselective catalysis 98. Preparation of 9-amino(9-deoxy)cinchona alkaloids

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
6
Issue
7
Identifiers
DOI: 10.1016/0957-4166(95)00215-b

Abstract

Abstract Cinchonine and quinine were allowed to react with hydrazoic acid in a Mitsunobu reaction to yield the corresponding azides with inversion of configuration at C9. In situ reduction of these azides provided 9-amino(9-deoxy)epicinchonine and 9-amino(9-deoxy)epiquinine, respectively. The structures were confirmed by CD-spectroscopy and X-ray crystallography.

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