Addition of aldehydes with allyltrichlorosilane catalyzed by chiral bis-N-O secondary amides
Deng, Yu1,2,3; Pan, Wei1,2,3; Pei, Yu-Ning1,2; Li, Jin-Liang1,2; Bai, Bing4; Zhu, Hua-Jie1,2,3
2013-12-02
发表期刊TETRAHEDRON
ISSN0040-4020
卷号69期号:48页码:10431-10437
摘要New axially N-oxide amides derived from L-tryptophan were prepared and used as organocatalysts in enantioselective allylation of aromatic aldehydes with allyltrichlorosilanes. The corresponding addition adducts homoallylic chiral alcohols obtained high enantioselectivities (up to 96% ee) when 1 mol % of catalyst was used. The unexpected result is the addition product's absolute configuration is R when (R)-chiral amides was used, in contrast, it was (S) when (R)-chiral methyl ester were used in allylation. It exhibited that the N atoms of amides take part in the transition state procedure. (C) 2013 Elsevier Ltd. All rights reserved.
关键词Bis-n-o Amides Allylation L-tryptophan Axial Ligand
资助信息Hebei University
收录类别SCI ; IC
语种英语
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/17448
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, Minist Educ, Chinese Ctr Chiral, Key Lab Med Chem & Mol Diag, Baoding 071002, Hebei, Peoples R China
2.Hebei Univ, Dept Chem & Chem Engn, Baoding 071002, Hebei, Peoples R China
3.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650204, Yunnan, Peoples R China
4.Zhengzhou Univ Light Ind, Sch Food & Biol Engn, Zhengzhou 450002, Peoples R China
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Deng, Yu,Pan, Wei,Pei, Yu-Ning,et al. Addition of aldehydes with allyltrichlorosilane catalyzed by chiral bis-N-O secondary amides[J]. TETRAHEDRON,2013,69(48):10431-10437.
APA Deng, Yu,Pan, Wei,Pei, Yu-Ning,Li, Jin-Liang,Bai, Bing,&Zhu, Hua-Jie.(2013).Addition of aldehydes with allyltrichlorosilane catalyzed by chiral bis-N-O secondary amides.TETRAHEDRON,69(48),10431-10437.
MLA Deng, Yu,et al."Addition of aldehydes with allyltrichlorosilane catalyzed by chiral bis-N-O secondary amides".TETRAHEDRON 69.48(2013):10431-10437.
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