Methods of Non-a-Amino Acid Synthesis, 2nd Edition

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Functional Group

Exchanges

1.1 REACTIONS WITH AMMONIA, AMINES,

OR AMINE SURROGATES

Incorporation of an amine moiety into a molecule by reaction with an alkyl halide

or an alkylsulfonate ester is a common synthetic method. This approach includes

reactions that produce amino acids, often using ammonia or amines as nucleophiles.

There are problems associated with such reactions, however, and several amine sur-

rogates have been developed that allow incorporation of nitrogen into the molecule,

and the amine moiety is unmasked later.

1.1.1 Reaction with ammonia

Amino acids can be prepared by the reaction of α-halo-carboxylic acid or a halo-car-