Abstract
Reacting imine derivatives of resin-bound amino acids with alpha,omega-dihaloalkanes provides highly versatile intermediates to racemic alpha,alpha-disubstituted amino acids with a wide variety of side-chain functionality. Two strategies were developed to convert the intermediate omega-chloro or omega-bromo derivatives to the desired products. Together, they allow the creation of amino acids with diverse functionalities (omega-chlorides, nitriles, azides, acetates, thioacetates, thioethers, secondary and tertiary aliphatic amines, and anilines) placed at varying chain lengths (2-5) from the alpha-center of the amino acid.
Publication types
-
Research Support, Non-U.S. Gov't
-
Research Support, U.S. Gov't, P.H.S.
MeSH terms
-
Alkylation
-
Amino Acids / chemistry
-
Amino Acids, Branched-Chain / chemical synthesis*
-
Amino Acids, Branched-Chain / chemistry*
-
Azides / chemistry
-
Catalysis
-
Chemistry, Organic / methods
-
Chromatography, High Pressure Liquid
-
Cyclization
-
Hydrocarbons, Halogenated / chemistry
-
Hydrolysis
-
Imines / chemistry
-
Lactones / chemistry
-
Magnetic Resonance Spectroscopy
-
Molecular Structure
-
Nitriles / chemistry
-
Proline / chemistry
-
Resins, Plant / chemistry
-
Temperature
Substances
-
Amino Acids
-
Amino Acids, Branched-Chain
-
Azides
-
Hydrocarbons, Halogenated
-
Imines
-
Lactones
-
Nitriles
-
Resins, Plant
-
Proline