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Simple synthetic route to polyhydroxylated pyrrolidines and piperidines
Author(s) -
Lee Sang Gyeong,
Yoon YongJin,
Park Ki Hun
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350334
Subject(s) - chemistry , regioselectivity , epoxide , intramolecular force , amination , ring (chemistry) , nucleophile , cleavage (geology) , lactone , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
A short and simple synthetic route to polyhydroxylated piperidines and pyrrolidines were described with D ‐glucurono‐δ‐lactone as chiral educt. Key reaction steps included selective cleavage of terminal isopropylidene group of compound 12 with Dowex 50W‐X8 resin (H + form), regioselective ring opening of epoxide 16 and intramolecular nucleophilic amination of compound 14 and 18 .
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