Aminocyclopropanecarboxylic acids derivatives, synthesis

Aminocyclopropanecarboxylic acid (74) has attracted special interest (a) as a modified model of natural a-amino acids, in the synthesis of bioactive peptide analogs, potential enzyme inhibitors , or e.g. a derivative with sweetness receptor activity s and (b) together with its Schiff-base metal complexesas the biosynthetic precursor of ethene, the plant ripening hormone . (See these sources and the review in Reference 135 for further references.)... 

Asymmetric cyclopropanation of a chiral azalactone 27, derived from 1,2-0-isopropyhdene-D-glyceraldehyde, was effected successfully with diazomethane in the synthesis of allocoronamic acid, one of the aminocyclopropanecarboxylic acids useful for the control of enzymatic pro-... 

The ylide from racemic (diethylamino)(methyl)(oxo)(phenyl)sulfonium tetrafluoroborate has been used to prepare cyclopropane derivatives required in the synthesis of several naturally occurring 1-aminocyclopropanecarboxylic acids. High diastereoselectivity combined with high yields (from optically active substrates) make this procedure attractive for cyclopropana-tion of alkenes. 

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