Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes

被引：9
|
作者：
Hojoh, Kentaro [1 ]
Shido, Yoshinori [1 ]
Nagao, Kazunori [1 ]
Mori, Seiji [2 ]
Ohmiya, Hirohisa [1 ]
Sawamura, Masaya [1 ]
机构：
[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
[2] Ibaraki Univ, Fac Sci, Mito, Ibaraki 3108512, Japan
来源：
TETRAHEDRON | 2015年 / 71卷 / 37期
基金：
日本学术振兴会; 日本科学技术振兴机构;
关键词：
Asymmetric catalysis; Copper catalyst; Allylic substitution; Alkylborane; Quaternary carbon; QUATERNARY STEREOGENIC CENTERS; CHIRAL DIPHOSPHINE LIGANDS; CONJUGATE ADDITION; ARYLBORONIC ACIDS; ORGANIC-SYNTHESIS; BEARING TERTIARY; SUBSTITUTION; REAGENTS; ALLYLSILANES; PHOSPHATES;
D O I：
10.1016/j.tet.2015.05.048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have presented full details of our work on alkylboranes, which we have introduced as new reagents for copper-catalyzed S(N)2'-type enantioselective allylic substitutions. The copper catalysis delivered enantioenriched chiral products containing tertiary or quaternary carbon stereogenic centers branched with functionalized sp(3)-alkyl groups. The wide availability of alkylboranes via the established alkene hydroboration reaction is an attractive feature of these transformations. Various functional groups are tolerated in the substrates. A reaction pathway involving addition elimination of a neutral alkylcopper(I) species with the ally! chloride substrate is proposed. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6519 / 6533
页数：15
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