Rhodium-Catalyzed Asymmetric 1,4-Addition of Heteroaryl Cyclic Triolborate to α,β-Unsaturated Carbonyl Compounds

被引：33

作者：

Yu, Xiao-Qiang ^{[1
]}

Yamamoto, Yasunori ^{[1
]}

Miyaura, Norio ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

来源：

SYNLETT | 2009年 / 06期

关键词：

heteroaryl cyclic triolborate; rhodium catalyst; asymmetric reaction; conjugate addition; ENANTIOSELECTIVE CONJUGATE ADDITION; ARYLBORONIC ACIDS; ENONES; ARYL; LIGANDS; ESTERS; COMPLEXES; EFFICIENT; DIETHYLZINC; REAGENTS;

D O I：

10.1055/s-0028-1088198

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-catalyzed asymmetric 1,4-additions of electron-deficient heteroaryl groups to alpha,beta-unsaturated carbonyl compounds were established. The reaction resulted in very low yields due to competitive C-B bond cleavage when arylboronic acids. their pinacol esters, or potassium trifluoroborates were used. However, the corresponding lithium heteroaryl(triol)borates afforded 1,4-adducts With high enantioselectivities up to 97% in the presence of a rhodium(I) catalyst chelated with a chiral BINAP or BIPAM ligand.

引用

页码：994 / 998

页数：5

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