中心金属或配体刚性调控的α-酮酸酯对硝基烯的不对称共轭加成

doi:10.1016/S1872-2067(14)60199-6

催化学报 ›› 2015, Vol. 36 ›› Issue (1): 57-67.DOI: 10.1016/S1872-2067(14)60199-6

中心金属或配体刚性调控的α-酮酸酯对硝基烯的不对称共轭加成

陈向宁, 周晗, 黄汉民

中国科学院兰州化学物理研究所羰基合成与选择性氧化国家重点实验室, 甘肃兰州730000

收稿日期:2014-05-15 修回日期:2014-06-15 出版日期:2014-12-31 发布日期:2014-12-31
通讯作者: 黄汉民
基金资助:
国家自然科学基金(21222203, 21172226和21133011).

Diastereo- and enantioselective conjugate addition of α-keto esters to nitroalkenes: Complete switch in the enantioselectivity by tuning the metal center or rigidity of the ligand

Xiangning Chen, Han Zhou, Hanmin Huang

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China

Received:2014-05-15 Revised:2014-06-15 Online:2014-12-31 Published:2014-12-31
Supported by:
This work was supported by the National Natural Science Foundation of China (21222203, 21172226, and 21133011).

摘要/Abstract

摘要：

通过手性二胺配体与Cu或Ni络合合成了手性金属催化剂, 并将其应用于α-酮酸酯对硝基烯的不对称共轭加成反应中, 发展了通过改变中心金属或调节配体刚性实现反应对映选择性反转的策略. 使用同一手性二胺配体(1S,1'S)-1,1'-联异吲哚啉, 与不同的金属前体(Cu(OAc)₂·H₂O与Ni(OAc)₂·4H₂O)络合, 可以高选择性地得到绝对构型相反的共轭加成产物(ee值高达94%与93%). 同样, 使用同一金属前体Cu(OAc)₂·H₂O, 与同一手性源出发合成的两种刚性不同的二胺配体络合, 也可以在这个反应中实现产物绝对构型的反转(ee值高达94%与94%).

关键词: 手性二胺, 共轭加成, 对映选择性, 中心金属, 配体刚性

Abstract:

A series of efficient catalytic systems has been developed to control the dual enantioselectivity of the conjugate addition of α-keto esters to nitroalkenes. The use of the chiral diamine (1S,1'S)-1,1'-biisoindoline as a chiral ligand with either (Cu(OAc)₂·H₂O or Ni(OAc)₂·4H₂O as the catalyst provide facile access to the respective enantiomers resulting from the conjugate addition reaction with high levels of enantioselectivity (94% ee vs 93% ee). Furthermore, the use of Cu(OAc)₂·H₂O as the metal center allowed the enantioselectivity of the conjugate addition reaction to be switched through the tuning of the rigidity of the chiral diamine ligand (94% ee vs 94% ee).

Key words: Chiral diamine, Conjugate addition, Dual enantioselectivity, Metal center, Rigid ligand

陈向宁, 周晗, 黄汉民. 中心金属或配体刚性调控的α-酮酸酯对硝基烯的不对称共轭加成[J]. 催化学报, 2015, 36(1): 57-67.

Xiangning Chen, Han Zhou, Hanmin Huang. Diastereo- and enantioselective conjugate addition of α-keto esters to nitroalkenes: Complete switch in the enantioselectivity by tuning the metal center or rigidity of the ligand[J]. Chinese Journal of Catalysis, 2015, 36(1): 57-67.

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中心金属或配体刚性调控的α-酮酸酯对硝基烯的不对称共轭加成

Diastereo- and enantioselective conjugate addition of α-keto esters to nitroalkenes: Complete switch in the enantioselectivity by tuning the metal center or rigidity of the ligand

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