A novel three-step hydroxy-deamination sequence: Conversion of lysine to 6-hydroxynorleucine derivatives

Oxidation of carbamates with catalytic RuO 4, generated from RuO 2 and NaBrO 3, provides the corresponding acyl carbamates, which can be reduced with NaBH 4 to provide alcohols. Application of this methodology to L-lysine provides ( S)-6-hydroxynorleucine derivatives. Graphic

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 32; pp. 5671 - 5674
Main Authors Nevill, C.Richard, Angell, Paul T.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.08.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYSTEM
L-ALPHA,OMEGA-DIAMINO ACIDS
RUTHENIUM TETROXIDE OXIDATION
ALPHA-AMINO ACIDS
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Summary:Oxidation of carbamates with catalytic RuO 4, generated from RuO 2 and NaBrO 3, provides the corresponding acyl carbamates, which can be reduced with NaBH 4 to provide alcohols. Application of this methodology to L-lysine provides ( S)-6-hydroxynorleucine derivatives. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01142-3