Chemical reactivity of 6-diazo-5-oxo- l-norleucine (DON) catalyzed by metalloporphyrins (Fe,Ru)

The transfer of the metallocarbene derived from N- and O-protected 6-diazo-5-oxo- l-norleucine (DON) catalyzed by metalloporphyrins undergoes dimerization, cyclopropanation, N–H and S–H insertion reactions, respectively. An efficient and direct synthesis of 5-oxo- l-pipecolic acid from DON is descri...

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Bibliographic Details
Published in:Tetrahedron 2010-06, Vol.66 (25), p.4462-4468
Main Authors: Le Maux, Paul, Nicolas, Irène, Chevance, Soizic, Simonneaux, Gérard
Format: Article
Language:English
Subjects:
6-Diazo-5-oxo- l-norleucine
Catalytic carbene transfer
Chemical reactivity
Chemical Sciences
Chemistry
Exact sciences and technology
Free radicals chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Iron porphyrin
Organic chemistry
Preparations and properties
Reactivity and mechanisms
Ruthenium porphyrin
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Summary:The transfer of the metallocarbene derived from N- and O-protected 6-diazo-5-oxo- l-norleucine (DON) catalyzed by metalloporphyrins undergoes dimerization, cyclopropanation, N–H and S–H insertion reactions, respectively. An efficient and direct synthesis of 5-oxo- l-pipecolic acid from DON is described from unprotected 6-diazo-5-oxo- l-norleucine. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.04.080