Structure influence of chiral 1,1 '-biscarboline-N,N '-dioxide on the enantioselective allylation of aldehydes with allyltrichlorosilanes
Bai, Bing2,3; Zhu, Hua-Jie1,2; Pan, Wei2
2012-08-26
发表期刊TETRAHEDRON
ISSN0040-4020
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
资助信息NSFC [30873141]; 973 program [2009CB522300]; Hebei University; Key State of Laboratory of Phytochemistry and Plant Resources in West Chian
DOI10.1016/j.tet.2012.06.042
收录类别SCI ; IC
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000306981800005
引用统计
被引频次:16[WOS]   [WOS记录]     [WOS相关记录]
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
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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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