Synthesis of α 2,2 ,β 3 ‐Diamino Acids by Double Stereodifferentiation Aldol Addition of Oxazolidinone Enolates to N ‐( tert ‐Butylsulfinyl) Imines

A novel application of Seebach's “SRS” synthetic principle works efficiently when conformationally restrained trisubstituted chiral α 2,2 ,β 3 ‐diamino acids are synthesized by double stereoinduction reactions of chiral oxazolidinone enolates with N ‐sulfinyl aldimines. Two stereoisomers were i...

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Bibliographic Details
Published in:European journal of organic chemistry 2008-08, Vol.2008 (22), p.3834-3844
Main Authors: Guerrini, Andrea, Varchi, Greta, Samorì, Cristian, Battaglia, Arturo
Format: Article
Language:English
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Summary:A novel application of Seebach's “SRS” synthetic principle works efficiently when conformationally restrained trisubstituted chiral α 2,2 ,β 3 ‐diamino acids are synthesized by double stereoinduction reactions of chiral oxazolidinone enolates with N ‐sulfinyl aldimines. Two stereoisomers were isolated in a form of 1′‐(sulfinylamino)oxazolidinones and bicyclic 1 H ,3 H ‐imidazo[1,5‐ c ]oxazole‐1,5(6 H )‐diones, from which the α 2,2 ,β 3 ‐diamino acids are obtained by selective deprotection methodologies. Among a variety of highly functionalized diamino acids, this highly diastereoselective protocol provides a synthetic route for yet unreported C ‐glycosyl and α‐nucleoside diamino acids. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800356