Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

被引：28

作者：

Michel, Nicholas W. M. ^{[1
]}

Jeanneret, Alexandria D. M. ^{[1
]}

Kim, Hyehwang ^{[1
]}

Rousseaux, Sophie A. L. ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

CROSS-COUPLING REACTIONS; ALPHA-ARYL NITRILES; C-O ACTIVATION; TRIMETHYLSILYL CYANIDE; BOND ACTIVATION; INTRAMOLECULAR ARYLCYANATION; ASYMMETRIC HYDROCYANATION; QUATERNARY STEREOCENTERS; KINETIC RESOLUTION; PALLADIUM-COMPLEX;

D O I：

10.1021/acs.joc.8b01763

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)(2). Alkene additives were found to inhibit catalysis, suggesting that avoiding beta-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (+/-)-naproxen from commercially available starting materials.

引用

页码：11860 / 11872

页数：13

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