Development of highly enantio selective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile

	Development of highly enantio selective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile
	Wu, PC; Wang, ZY; Cheng, MN; Zhou, L; Sun, J; Sun, J, Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China.
刊名	TETRAHEDRON
	2008
卷号	64 期号:49 页码:11304_11312
关键词	Lewis Basic Organocatalysts Acyclic Ketimines L-pipecolinic Acid Asymmetric Reduction
ISSN号	0040-4020
产权排序	1
英文摘要	L-Pipecolinic acid derived N-formamides have been developed as new Lewis basic organocatalysts that promote the asymmetric reduction of N-aryl ketimines using trichlorosilane as the reducing agent. The substituent on N4 of the piperazinyl backbone and the 2-carboxamide group both proved to have profound effects on the efficacy of the catalyst. The reductions of both N-aryl acyclic methyl ketimines and non-methyl ketimines were catalyzed to afford the desired amines in good to high yield and enantioselectivity. In particular, catalyst 6e enabled the reduction of the difficult bulky ketimines to be highly efficient and enantioselective, affording up to 99% yield and 97% ee. This catalyst proved to prefer the relatively bulkier non-methyl acyclic ketimines to the methyl ketimines as substrate, which is so far unprecedented in catalytic asymmetric reduction of imines. (C) 2008 Elsevier Ltd. All rights reserved.
学科主题	Chemistry, Organic
语种	英语
WOS记录号	WOS:000261416900046
资助机构	National Natural Science Foundation of China [20672107, 20732006] ; National Natural Science Foundation of China [20672107, 20732006] ; National Natural Science Foundation of China [20672107, 20732006] ; National Natural Science Foundation of China [20672107, 20732006]
公开日期	2011-07-08
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/18083]
专题	成都生物研究所_天然产物研究
通讯作者	Sun, J, Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China.
推荐引用方式 GB/T 7714	Wu, PC,Wang, ZY,Cheng, MN,et al. Development of highly enantio selective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile[J]. TETRAHEDRON,2008,64(49):11304_11312.
APA	Wu, PC,Wang, ZY,Cheng, MN,Zhou, L,Sun, J,&Sun, J, Chinese Acad Sci, Chengdu Inst Biol, Nat Prod Res Ctr, Chengdu 610041, Peoples R China..(2008).Development of highly enantio selective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile.TETRAHEDRON,64(49),11304_11312.
MLA	Wu, PC,et al."Development of highly enantio selective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile".TETRAHEDRON 64.49(2008):11304_11312.