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
Corresponding AuthorZhu, 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
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume68Issue:34Pages:6829-6836
AbstractA 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.
KeywordBiscarboline Allylation n Enantioselective Catalysis n '-dioxide
DOI10.1016/j.tet.2012.06.042
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000306981800005
Citation statistics
Cited Times:16[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/15712
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
Recommended Citation
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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