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.

New Perspectives in Lithium Carbenoid Mediated Homologations / V. Pace, L. Castoldi, S. Monticelli, M. Rui, S. Collina. - In: SYNLETT. - ISSN 0936-5214. - 28:8(2017 May), pp. st-2016-p0838-sp.879-st-2016-p0838-sp.888. [10.1055/s-0036-1588139]

New Perspectives in Lithium Carbenoid Mediated Homologations

L. Castoldi
Secondo
;
2017

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.
carbenoids; lithium; homologation; chemoselectivity; organometallic reagents;
Settore CHIM/06 - Chimica Organica
1-feb-2017
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890715
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