Enantio- and Regioconvergent Nickel-Catalyzed C(sp3)-C(sp3) Cross-Coupling of Allylic Electrophiles Steered by a Silyl Group

被引：17

作者：

Kranidiotis-Hisatomi, Nektarios ^{[1
]}

Yi, Hong ^{[1
]}

Oestreich, Martin ^{[1
]}

机构：

[1] Tech Univ Berlin, Inst Chem, Str 17 Juni 115, D-10623 Berlin, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 24期

关键词：

cross-coupling; nickel; radical reactions; silicon; synthetic methods;

D O I：

10.1002/anie.202102233

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A two-step sequence for the enantio- and diastereoselective synthesis of exclusively alkyl-substituted acyclic allylic systems with a stereocenter in the allylic position is reported. The asymmetric induction and the site selectivity are controlled in an enantio- and regioconvergent nickel-catalyzed C(sp(3))-C(sp(3)) cross-coupling of regioisomeric mixtures of racemic alpha-/gamma-silylated allylic halides and primary alkylzinc reagents. The silyl group steers the allylic displacement towards the formation of the vinylsilane regioisomer, and the resulting C(sp(2))-Si bond serves as a linchpin for the installation of various C(sp(3)) substituents in a subsequent step.

引用

页码：13652 / 13655

页数：4

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