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Epimerization of the α Stereocenter in d ‐Ribose‐Derived Nitrones: Direct Access to Variant Quinolizidines with d ‐Ribo and d ‐Arabino Configurations
Author(s) -
Rowicki Tomasz,
Malinowski Maciej,
Łapczyński Sebastian,
Gryszel Maciej,
Czerwińska Karolina,
Madura Izabela,
Sas Wojciech
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500118
Subject(s) - epimer , chemistry , stereocenter , stereochemistry , tautomer , nitrone , organic chemistry , enantioselective synthesis , catalysis , cycloaddition
Abstract The concise synthesis of two polyhydroxyquinolizidines from 2,3‐ O ‐isopropylidene‐ d ‐ribofuranose was accomplished. Epimerization of the intermediate N ‐(3‐ a lkenyl)nitrone resulted in exceptionally straightforward access to an iminosugar with a d ‐arabino configuration. A plausible mechanism of the epimerization via nitrone‐enehydroxylamine tautomerism explaining the reaction course has been proposed.