Literature DB >> 14505383

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

Mukund P Sibi1, Narayanasamy Prabagaran, Sandeep G Ghorpade, Craig P Jasperse.   

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.

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Year:  2003        PMID: 14505383     DOI: 10.1021/ja0372309

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  14 in total

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Authors:  Jonathan E Wilson; Anthony D Casarez; David W C MacMillan
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