New Perspectives in Lithium Carbenoid Mediated Homologations

Vittorio Pace; Laura Castoldi; Serena Monticelli; Marta Rui; Simona Collina

doi:10.1055/s-0036-1588139

Synlett, Table of Contents

Synlett 2017; 28(08): 879-888
DOI: 10.1055/s-0036-1588139

synpacts

New Perspectives in Lithium Carbenoid Mediated Homologations

Authors

Vittorio Pace*

^aDepartment of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria Email: vittorio.pace@univie.ac.at
Laura Castoldi

^aDepartment of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria Email: vittorio.pace@univie.ac.at
Serena Monticelli

^aDepartment of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria Email: vittorio.pace@univie.ac.at
Marta Rui

^aDepartment of Pharmaceutical Chemistry, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria Email: vittorio.pace@univie.ac.at

^bDepartment of Drug Sciences, University of Pavia, Viale Taramelli 6, 27100, Pavia, Italy
Simona Collina

^bDepartment of Drug Sciences, University of Pavia, Viale Taramelli 6, 27100, Pavia, Italy

Abstract

All articles of this category

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

Key words

carbenoids - lithium - homologation - chemoselectivity - organometallic reagents

Full Text

References

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