Stereoselective SN1-Type Reaction of Enols and Enolates

被引：22

作者：

Gualandi, Andrea ^{[1
]}

Mengozzi, Luca ^{[1
]}

Cozzi, Pier Giorgio ^{[1
]}

机构：

[1] ALMA MATER STUDIORUM Univ Bologna, Dipartimento Chim G Ciamician, Via Selmi 2, I-40126 Bologna, Italy

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 15期

关键词：

enolates; stereoselectivity; SN1; reactions; carbenium ions; Mayr scale; PROPARGYLIC SUBSTITUTION-REACTIONS; BETA-DICARBONYL COMPOUNDS; DIRECT ALPHA-ALKYLATION; BRONSTED ACID; ORGANOCATALYTIC ALKYLATION; NUCLEOPHILIC-SUBSTITUTION; ASYMMETRIC ALKYLATION; CATALYZED ADDITION; METAL-CATALYSTS; ALCOHOLS;

D O I：

10.1055/s-0036-1588871

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective alkylation of enolates represents a valuable and important procedure for accessing carbon-carbon-bond frameworks in natural and nonnatural product synthesis. Usually, activated electrophilic partners that react through an SN2 mechanism are employed. To overcome the limitations due to reduced reactivity and steric hindrance, SN1-type reactions can be considered a valid and practical alternative. Accessible enolates can be used in stereoselective (diastereo- or enantioselective) reactions with electrophilic carbenium ions, either used as stable reagents or generated in situ from suitable precursors. The results achieved in this active field are summarized in this review.

引用

页码：3433 / 3443

页数：11

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