Lorna Conway, P. Evans
Oct 29, 2021
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Journal
Journal of Chemical Research
Abstract
Routes are reported for the synthesis of both (1R)- and (1S)-tert-butyl-(4-oxocyclopent-2-en-1-yl)carbamate 2. Featuring Mitsunobu reactions with di-tert-butyl iminodicarbonate, both syntheses begin from (S)-4-[(tert-butyldimethylsilyl)oxy]cyclopent-2-en-1-one (3) and take advantage of the 1,4-cyclopentenyl dioxygenation pattern of this optically active starting material. Thus both (−)- and (+)-2 have been accessed from 3 in an enantiodivergent manner in 11% and 10% overall yield over five and seven reaction steps, respectively.