Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: Application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones

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Abstract

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 α-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. © 2010 Elsevier Ltd. All rights reserved.

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Yang, T. F., Shen, C. H., Hsu, C. T., Chen, L. H., & Chuang, C. H. (2010). Selective reaction of camphor-derived exo-formyl [2.2.1]bicyclic carbinol with alkyl primary amines: Application to the preparation of new chiral catalysts for asymmetric reduction of aryl ketones. Tetrahedron, 66(45), 8734–8738. https://doi.org/10.1016/j.tet.2010.09.008

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