Acta Phys. -Chim. Sin. ›› 2002, Vol. 18 ›› Issue (10): 890-895.doi: 10.3866/PKU.WHXB20021005

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Quantum Chemical Study on the Mechanism of Enantioselective Alkynylation of

Li Ming;He Rong-Xing   

  1. College of Chemistry and Chemical Engineering, Southwest-China Normal University, Chongqing 400715
  • Received:2001-12-25 Revised:2002-04-05 Published:2002-10-15
  • Contact: Li Ming E-mail:liming@swnu.edu.cn

Abstract: The semi empirical molecular orbital computations of the enontioselective alkynylation of benzaldehyde catalyzed by oxazaborolidine catalysts are performed. As illustrated, this enantioselective alkynylation reduction is exothermic and the controlling step is the transfer of alkynyl from the alkynylborane moiety to the carbonyl carbon of benzaldehyde. The transition state for the alkynyl transfer is a twisted chair structure. The alkynyl reduction leads to R-chiral alcohols.

Key words: Chiral oxazaborolidine, Enantioselective alkynylation, Semiempirical method, Benzaldehyde