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
Corresponding AuthorZhu,HJ (reprint author),Hebei Univ,Minist Educ,Chinese Ctr Chiral,Key Lab Med Chem & Mol Diag,Baoding 071002,Hebei,Peoples R China. ; zhuhua-jie@hotmail.com
2013-12-02
Source PublicationTETRAHEDRON
ISSN0040-4020
Volume69Issue:48Pages:10431-10437
AbstractNew 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.
KeywordBis-n-o Amides Allylation L-tryptophan Axial Ligand
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000328521700031
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/17448
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, 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
Recommended Citation
GB/T 7714
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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