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Synfacts 2006(3): 0248-0248
DOI: 10.1055/s-2006-931953
DOI: 10.1055/s-2006-931953
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Addition of Propargylic Copper Oxazolidinones to Aldehydes
N. Alouane, F. Bernaud, J. Marrot, E. Vrancken*, P. Mangeney*
Université Pierre et Marie Curie, Paris and Université de Versailles, France
Further Information
Publication History
Publication Date:
21 February 2006 (online)
Significance
The copper reagent derived from enantiopure propargylic oxazolidinone reacted regio- and diastereoselectively with aldehydes to give anti-homopropargylic amino alcohols. This is a one-pot procedure made possible by transmetallation of the lithiated species to the organocopper reagent. The stereochemistry of the major product obtained is complementary to Hegedus’ tin chemistry. In most cases, no syn isomer was observed.