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Chem. J. Chinese Universities ›› 2000, Vol. 21 ›› Issue (S1): 438.

• Synthetic Sciences • Previous Articles     Next Articles

Highly Efficient Enantioselective Synthesis of Optically Active Dihydropyrones by Chiral Titanium(IV) (5,5',6,6',7,7',8,8'-Octahydro-1,1'-Bi-2-Naphthol) Complexes

FENG Xiao-Ming1, WANG Bin2, CUI Xin2, LIU Hui2, JIANG Yao-Zhong2   

  1. 1. The Faculty of Chemistry, Sichuan University, Chengdu 610064;
    2. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041
  • Online:2000-12-31 Published:2000-12-31
  • Supported by:

    We are grateful for the financial support from the National Science Foundation of China (No. 29832020).

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Abstract:

The formal hetero-Diels-Alder reaction between 1-methoxy-3-(trimethyl-silyl)oxy-1,3-butadiene and aldehydes provides useful access to dihydropyrones, a class of compounds with extensive utility in organic synthesis. Asymmetric catalysis of this reaction has been previously reported by a number of investigators. Herein we wish to describe that chiral 5,5',6,6',7,7',8,8'-octahydro-1, 1'-bi-2-naphthol (H8-BINOL)/Ti(O-i-Pr)4 complexes are more effective catalysts than BINOL/Ti(O-i-Pr)4 and others for the asymmetric hetero-Diels-Alder reactions.

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