Taylor and Francis Group, Synthetic Communications, 17(44), p. 2510-2519
DOI: 10.1080/00397911.2014.905601
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Synthesis of cyclic α-hydrazino acids of 5, 6, 7, 8, and 9-membered rings has been described. Di-tert-butyl or dibenzyl malonate was used as starting materials instead of diethyl malonate which was used in our first report. Deprotection of tert-butyl or benzyl ester of the final compounds was much easier than ethyl or methyl esters. Overall yield of these acids were 39, 50, 47, 52, 51 %, respectively. These acids were then converted to the diastereomers either via the formation of peptides with L-phenylalanine methyl ester or via the formation of esters (for 5 to 7-memebered rings) with L-2-phenylalaninol. All diastereomers were separated except 9-membered ring by flash chromatography. Hydrolysis of diastereomeric esters generated the optically pure 5, 6 and 7-membered cyclic α-hydrazino acids. In this process, both the enantiomers have been isolated and recovered the chiral auxiliary L-2-phenylalaninol. Absolute stereochemistry was determined from X-ray crystallographic analysis