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Synlett 2017; 28(08): 879-888
DOI: 10.1055/s-0036-1588139
DOI: 10.1055/s-0036-1588139
synpacts
New Perspectives in Lithium Carbenoid Mediated Homologations
Weitere Informationen
Publikationsverlauf
Received: 11. Dezember 2016
Accepted after revision: 09. Januar 2017
Publikationsdatum:
01. Februar 2017 (online)
Dedicated to Professor Friedrich Hammerschmidt on the occasion of his retirement
Abstract
α-Functionalized organolithium reagents (e.g., LiCH2X) are versatile reagents for accomplishing homologations of carbon- and heteroatom-type electrophiles. The proper selection of the reaction conditions allows one to direct their intrinsic ambiphilicity towards the nucleophilic character. Herein, the homologation of various electrophiles ranging from Weinreb amides to isocyanates, carbonyl derivatives, and chalcogenides – with a particular focus on the chemoselectivity of the processes – is summarized.
1 Introduction
2 Homologation of Weinreb Amides
3 Homologation of Cyclic Ketones
4 Homologation of Isocyanates
5 Homologation of Disulfides and Diselenides
6 Conclusions
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