Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes

doi:10.1016/j.tet.2012.06.042

	Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes
	Bai, Bing 2,3; Zhu, Hua-Jie 1,2; Pan, Wei 2
通讯作者	Zhu, HJ (reprint author), Hebei Univ, Coll Life Sci, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China.,zhuhuajie@hotmail.com
	2012-08-26
发表期刊	TETRAHEDRON
ISSN	0040-4020
卷号	68 期号:34 页码:6829-6836
摘要	A series of new axially chiral 1,1'-biscarboline-N,N'-dioxide Lewis base organocatalysts were examined in the asymmetric allylation of aldehydes with allyltrichlorosilane. The chiral catalysts (R)-1a-e bearing ester groups in 3,3' position provided good yields of the homoallyl alcohols with excellent enantioselectivities up to 99% for a broad substrate scope that covers aliphatic, aromatic, heteroaromatic, and alpha,beta-unsaturated aldehydes. Solvent effects on the conversion and enantioselectivity were elucidated, and CH2Cl2 proved to be the optimal solvent for the reactions. In addition, the allylation with crotyltrichlorosilane was explored and the result showed that anti-isomer was favored from (E)-crotyltrichlorosilane with complete diastereoselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
关键词	Biscarboline Allylation n Enantioselective Catalysis n '-dioxide
DOI	10.1016/j.tet.2012.06.042
收录类别	SCI ; IC
语种	英语
WOS记录号	WOS:000306981800005
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/15712
专题	植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.Hebei Univ, Coll Life Sci, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Peoples R China 3.Zhengzhou Univ Light Ind, Sch Food & Biol Engn, Zhengzhou 450002, Peoples R China 4.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Bai, Bing,Zhu, Hua-Jie,Pan, Wei. Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes[J]. TETRAHEDRON,2012,68(34):6829-6836.
APA	Bai, Bing,Zhu, Hua-Jie,&Pan, Wei.(2012).Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes.TETRAHEDRON,68(34),6829-6836.
MLA	Bai, Bing,et al."Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes".TETRAHEDRON 68.34(2012):6829-6836.

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