Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes

被引：13

作者：

Yasuda, Yuto ^{[1
]}

Nagao, Kazunori ^{[1
]}

Shido, Yoshinori ^{[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：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 27期

关键词：

allylic substitution; copper catalysis; coupling; secondary alkylborane; stereoselectivity; CARBON STEREOGENIC CENTERS; CONJUGATE ADDITION; ORGANIC-SYNTHESIS; BEARING TERTIARY; SUBSTITUTION; PHOSPHATES; ALLYLSILANES; REAGENTS; ARYL; ALKYLATIONS;

D O I：

10.1002/chem.201501055

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The scope of the copper-catalyzed coupling reactions between organoboron compounds and allylic phosphates is expanded significantly by employing triphenylphosphine as a ligand for copper, allowing the use of secondary alkylboron compounds. The reaction proceeds with complete gamma-E-selectivity and preferential 1,3-syn stereoselectivity. The reaction of gamma-silicon-substituted allylic phosphates affords enantioenriched alpha-stereogenic allylsilanes.

引用

页码：9666 / 9670

页数：5

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