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

  • Yang T
  • Shen C
  • Hsu C
 et al. 
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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 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.

Author-supplied keywords

  • Asymmetric reduction of ketone
  • Bicyclic amino ketone
  • Chiral catalyst
  • Ring expansion

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  • Te Fang Yang

  • Chien Hung Shen

  • Chi Tung Hsu

  • Li Hsun Chen

  • Chih Hsiang Chuang

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