3,4-O-Isopropylidene-3(R),4(S)-dihydroxycyclohexanone, a chiron easily prepared through a five step sequence from D(-)-quinic acid, has been efficiently utilized as the starting building block for the enantioselective syntheses of (3R,4S)-N-p-toluenesulfonyl-3,4-epoxy-hexahydroazepine and (1R,4S)-N-tert-butoxycarbonyl-7-azabicyclo[2.2.1]heptan-2-one, advanced intermediates already taken to (-)-balanol and (-)-epibatidine respectively.
A unified asymmetric approach to substituted hexahydroazepine and 7-azabicyclo[2.2.1] heptane ring systems from D-(-)-Quinic acid: application to the formal syntheses of (-)-Balanol and (-)-Epibatidine.
BARCO, Achille;BENETTI, Simonetta;DE RISI, Carmela;POLLINI, Gian Piero;ZANIRATO, Vinicio
1997
Abstract
3,4-O-Isopropylidene-3(R),4(S)-dihydroxycyclohexanone, a chiron easily prepared through a five step sequence from D(-)-quinic acid, has been efficiently utilized as the starting building block for the enantioselective syntheses of (3R,4S)-N-p-toluenesulfonyl-3,4-epoxy-hexahydroazepine and (1R,4S)-N-tert-butoxycarbonyl-7-azabicyclo[2.2.1]heptan-2-one, advanced intermediates already taken to (-)-balanol and (-)-epibatidine respectively.File in questo prodotto:
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