Literature DB >> 17581658

Diastereoselective synthesis of quaternary alpha-amino acids from diketopiperazine templates.

Stephen G Davies1, A Christopher Garner, Jaqueline V A Ouzman, Paul M Roberts, Andrew D Smith, Emma J Snow, James E Thomson, Juan A Tamayo, Richard J Vickers.   

Abstract

Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6-dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary alpha-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis.

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Year:  2007        PMID: 17581658     DOI: 10.1039/b704475e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  6'-Oxa Analogs of S-Adenosylhomocysteine.

Authors:  Weikuan Li; Wei Ye; Stewart W Schneller
Journal:  Tetrahedron       Date:  2012-01-07       Impact factor: 2.457

2.  Potassium [1-(tert-but-oxy-carbon-yl)-1H-indol-3-yl]trifluoro-borate hemihydrate.

Authors:  Guillaume Berionni; Peter Mayer; Herbert Mayr
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-06

3.  One-pot Ugi/Aza-Michael synthesis of highly substituted 2,5-diketopiperazines with anti-proliferative properties.

Authors:  Andreas Hartung; Florian Seufert; Carsten Berges; Viktoria H Gessner; Ulrike Holzgrabe
Journal:  Molecules       Date:  2012-12-11       Impact factor: 4.411

  3 in total

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