Synthesis of Novel Tartaric Acid-derived Chiral Phosphite Ligands and Their Application in the Cu-catalyzed Conjugate Addition of Diethylzinc to Cyclic Enones

doi:10.1007/s40242-015-5142-y

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (5): 756-760.doi: 10.1007/s40242-015-5142-y

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Synthesis of Novel Tartaric Acid-derived Chiral Phosphite Ligands and Their Application in the Cu-catalyzed Conjugate Addition of Diethylzinc to Cyclic Enones

PANG Zengbo^1,2, XING Aiping^1,2, WANG Lailai¹

1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100039, P. R. China

Received:2015-04-08 Revised:2015-05-08 Online:2015-10-01 Published:2015-06-29
Contact: WANG Lailai, E-mail: wll@licp.cas.cn E-mail:wll@licp.cas.cn
Supported by:
Supported by the National Natural Science Foundation of China (Nos.20773147, 21073211, 21174155).

Abstract

Abstract:

Five novel tropos (3R,4R)- and/or (3S,4S)-N-benzyltartarimide-derived biphenylphosphite ligands were synthesized and applied in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to cyclic enones with up to 75% e.e. Compared with the reported ligand 1-N-benzylpyrrolidine-3,4-bis[(R)-1,1'-binaphthyl-2,2'-diyl]phosphite-L-tartaric acid, the issue that L-(+)-tartaric acid backbone and (R)-binaphthyl showed strong matched/mismatched character was solved with these tropos ligands. It was found that the enantioselectivity was mainly controlled by the absolute configuration of N-benzyltartarimide backbone, and both enantiomers of the addition products can be obtained by simply changing the configuration of N-benzyltartarimide substituent.

Key words: L-(+)- and/or D-(?)-tartaric acid, Phosphite ligand, 1,4-Conjugate addition, Copper salt, Cyclic enone

PANG Zengbo, XING Aiping, WANG Lailai. Synthesis of Novel Tartaric Acid-derived Chiral Phosphite Ligands and Their Application in the Cu-catalyzed Conjugate Addition of Diethylzinc to Cyclic Enones[J]. Chemical Research in Chinese Universities, 2015, 31(5): 756-760.

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Synthesis of Novel Tartaric Acid-derived Chiral Phosphite Ligands and Their Application in the Cu-catalyzed Conjugate Addition of Diethylzinc to Cyclic Enones

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