Cyclic sulfamidates, 1  , bearing nitrogen atom as a part of the five-membered ring system are synthetic equivalent of aziridines 2  with certain advantages in terms of ring opening reactions namely, a) They have only one preferred site of attack  (C1  ) towards the incoming nucleophiles whereas such reactions in aziridines are dependent on the size of R1  and R2;  b) The reactivity of sulfamidates is independent of the nature of N-protecting group used; in contrast, the aziridines are classified as activated and non-activated based on R-group attached to the nitrogen atom. In view of the limited applications of sulfamidates in organic synthesis and in our quest for development of greener methodology, herein we describe a simple and high yielding protocol for the synthesis of chiral triazole-based unnatural amino acids using sulfamidates. This one-pot multi-component reaction proceeds via regioselective ring opening of sulfamidate with NaN3 followed by Cu-azide-alkyne cycloaddition reaction

Synthesis of triazole-based unnatural amino acids via regioselective ring opening of sulfamidates

243rd National Meeting (2012)

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