Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles

被引：51

作者：

Zi, You ^{[1
]}

Lange, Markus ^{[1
]}

Schultz, Constanze ^{[1
]}

Vilotijevic, Ivan ^{[1
]}

机构：

[1] Friedrich Schiller Univ Jena, Inst Organ Chem & Macromol Chem, Humboldtstr 10, D-07743 Jena, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 31期

关键词：

allylation; latent nucleophiles; Lewis base catalysis; nitrogen heterocycles; nucleophilic substitution; BAYLIS-HILLMAN ADDUCTS; ALLYLIC ALKYLATION; KINETIC RESOLUTION; CONTROLLED SWITCH; CARBONATES; FLUORIDES; AMINATION; REGIOSELECTIVITY; SUBSTITUTION; DERIVATIVES;

D O I：

10.1002/anie.201903392

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, indoles, and carbazoles serve as latent N-centered nucleophiles in substitution reactions of allylic fluorides catalyzed by Lewis bases. The reactions feature broad scopes for both reaction partners, excellent regioselectivities, and produce enantioenriched N-allyl pyrroles, indoles, and carbazoles when chiral cinchona alkaloid catalysts are used.

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收藏

页码：10727 / 10731

页数：5

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