Title
Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles
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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.
Object type
Language
English [eng]
Persistent identifier
https://phaidra.univie.ac.at/o:561932
Appeared in
Title
Chemical Communications
Volume
53
Issue
68
From page
9498
To page
9501
Publisher
Royal Society of Chemistry (RSC)
Date issued
2017
Access rights
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