Asymmetric Dimerization of Disubstituted Ketenes Catalyzed by N-Heterocyclic Carbenes

被引:72
作者
Lv, Hui [1 ]
Zhang, Yan-Rong [1 ]
Huang, Xue-Liang [1 ]
Ye, Song [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Biol Chem Lab, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
关键词
asymmetric catalysis; carbenes; dimerization; ketenes; lactones;
D O I
10.1002/adsc.200800532
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A series of chiral N-heterocyclic carbenes (NHCs), derived from L-pyrOgutamic acid, were found to be efficient catalysts for the asymmetric dirnerization of alkylarylketenes to give the corresponding alpha-quaternary beta-alkylidenyl-beta-lactones in good yields with up to 97% ee. A chiral NHC with a proximal hydroxy group is superior in comparison with the corresponding NHC with its hydroxy group protected.
引用
收藏
页码:2715 / 2718
页数:4
相关论文
共 31 条
[31]   Chiral N-heterocyclic carbene catalyzed Staudinger reaction of ketenes with imines:: Highly enantioselective synthesis of N-boc β-lactams [J].
Zhang, Yan-Rong ;
He, Lin ;
Wu, Xu ;
Shao, Pan-Lin ;
Ye, Song .
ORGANIC LETTERS, 2008, 10 (02) :277-280