C2 symmetric chiral NHC ligand for asymmetric quaternary carbon constructing copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclohexenones

被引：114

作者：

Matsumoto, Yasumasa ^{[1
]}

Yamada, Ken-ichi ^{[1
]}

Tomioka, Kiyoshi ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Kyoto 6068501, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 12期

关键词：

D O I：

10.1021/jo800613h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric construction of quaternary carbon centers by conjugate addition of Grignard reagents to 3-methyl- and 3-ethylcyclohexenones was realized in a maximum enantioselectivity of 80% by using a C(2) symmetric chiral N-heterocyclic carbene (NHC)-copper catalyst, generated from (4S,5S)-1,3-bis(2-methoxyphenyl)-4,5-diphenyl-4,5-dihydro-1H-imidazol-3-ium tetrafluoroborate and copper(II) triflate. The stereostructures of the NHC-Au complexes were analyzed by X-ray crystallography, which rationalized the good stereocontrolling ability of N-aryl NHCs.

引用

页码：4578 / 4581

页数：4

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