Exploiting [2+2] cycloaddition chemistry: achievements with allenes

被引：337

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro ^{[2
]}

Aragoncillo, Cristina ^{[1
]}

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

CHEMICAL SOCIETY REVIEWS | 2010年 / 39卷 / 02期

关键词：

DI-PI-METHANE; THERMALLY UNSTABLE ALLENES; RADICAL-CHAIN ADDITION; ALLENYL(VINYL)METHANE PHOTOCHEMISTRY. PHOTOCHEMISTRY; BENZANNULATED ENYNE-ALLENES; STEREOCHEMICAL FEATURES; ENANTIOENRICHED 1,3-DIMETHYLALLENE; SUBSTITUTED ALLENES; CHIRAL ALLENES; ALPHA; BETA-UNSATURATED KETONES;

D O I：

10.1039/b913749a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The allene moiety represents an excellent partner for the [2+2] cycloaddition with alkenes and alkynes, affording the cyclobutane and cyclobutene skeletons in a single step. This strategy has been widely studied under thermal, photochemical and microwave induced conditions. More recently, the use of transition metal catalysis has been introduced as an alternative relying on the activation of the allenic component. On the other hand, the intramolecular version has attracted much attention as a strategy for the synthesis of polycyclic compounds in a regio- and stereoselective fashion. This critical review focuses on the most recently developed [2+2] cycloadditions on allenes along with remarkable early works accounting for the mechanism, the regio- and diastereoselectivity of the cycloadducts formed (103 references).

引用

页码：783 / 816

页数：34

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