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J Am Chem Soc. 2003 Oct 1;125(39):11796-7.

Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids.

Author information

1
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105, USA.

Abstract

Highly diastereoselective and enantioselective addition of N-benzylhydroxylamine to imides 17 and 20-30 produces alpha,beta-trans-disubstituted N-benzylisoxazolidinones 19 and 31-41. These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids.

PMID:
14505383
DOI:
10.1021/ja0372309
[Indexed for MEDLINE]

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