Enantioselective addition of oxazolones to N-protected imines catalysed by chiral thioureasElectronic supplementary information (ESI) available: Experimental procedures, characterisation data, and computational details. See DOI: 10.1039/c5ra00092k

Hydrogen bond-catalysed aza-Mannich addition of oxazolones to various protected aldimines has been developed. The resulting, highly functionalized, oxazolones contain a quaternary stereogenic centre and can serve as precursors for chiral α,β-diamino acids with different protecting groups on each ami...

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Main Authors: abka, Matej, Malastová, Andrea, Šebesta, Radovan
Format: Article
Language:English
Online Access:Get full text
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Summary:Hydrogen bond-catalysed aza-Mannich addition of oxazolones to various protected aldimines has been developed. The resulting, highly functionalized, oxazolones contain a quaternary stereogenic centre and can serve as precursors for chiral α,β-diamino acids with different protecting groups on each amino group. The process benefits from the versatile bifunctional thiourea catalysts, which effect the formation of these products in high yields and stereoselectivities. Chiral thiourea-catalysed Mannich-type addition of oxazolones to imines, which provide highly functionalized amino oxazolones with quaternary stereogenic centres.
ISSN:2046-2069
DOI:10.1039/c5ra00092k