Abstract
[reaction: see text] A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5]decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-gamma-amino acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Amino Acids / chemical synthesis*
-
Amino Acids / chemistry
-
Epoxy Compounds / chemical synthesis*
-
Epoxy Compounds / chemistry
-
Lithium / chemistry*
-
Nitrogen Oxides / chemistry*
-
Oxazines / chemical synthesis*
-
Oxazines / chemistry
-
Oxazoles / chemistry*
-
Stereoisomerism
Substances
-
Amino Acids
-
Epoxy Compounds
-
Nitrogen Oxides
-
Oxazines
-
Oxazoles
-
nitrones
-
Lithium