Journal
TETRAHEDRON
Volume 66, Issue 45, Pages 8734-8738Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.09.008
Keywords
Ring expansion; Bicyclic amino ketone; Chiral catalyst; Asymmetric reduction of ketone
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Funding
- National Science Council of Taiwan [NSC 96-2113-M-324-001]
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Reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with various alkyl primary amines gave regio- and stereo-specific [3.2.1]bicyclic alpha-amino ketones. A detailed mechanism of the reaction was discussed. This reaction was further applied to the preparation of some camphor-derived oxazaborolidines, one of which proved to be an efficient chiral catalyst for the asymmetric borane reduction of prochiral aryl ketones at room temperature. (C) 2010 Elsevier Ltd. All rights reserved.
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