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.

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, V. Pace. - In: CHEMICAL COMMUNICATIONS. - ISSN 1359-7345. - 53:68(2017 Sep 04), pp. 9498-9501. [10.1039/c7cc05215d]

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

L. Castoldi
Primo
;
2017

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.
Settore CHIM/06 - Chimica Organica
1-ago-2017
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890719
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