Issue 68, 2017

Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles

Abstract

The tetrahedral intermediates generated upon the addition of halolithium carbenoids (LiCH2X and LiCHXY) to Weinreb amides have been intercepted and fully characterized as O-TMS heminals. The commercially available N-trimethylsilyl imidazole is the ideal trapping agent whose employment, combined with a straightforward neutral Alox chromatographic purification, enables the isolation of such labile species. The procedure could be advantageously extended also for obtaining O-TMS heminals from N-acylpyrroles. These intermediates manifest interesting reactivity including as precursors of more complex carbenoids.

Graphical abstract: Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles

Supplementary files

Article information

Article type
Communication
Submitted
06 Jul 2017
Accepted
31 Jul 2017
First published
01 Aug 2017
This article is Open Access
Creative Commons BY license

Chem. Commun., 2017,53, 9498-9501

Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles

L. Castoldi, W. Holzer, T. Langer and V. Pace, Chem. Commun., 2017, 53, 9498 DOI: 10.1039/C7CC05215D

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