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Stereoselective Synthesis of Piperidine Alkaloid (+)‐α‐Conhydrine and Its Pyrrolidine Analogue
Author(s) -
Jin Tian,
Mu Yu,
Kim GunWoo,
Kim SungSoo,
Kim JinSeok,
Huh SungIl,
Lee KeeYoung,
Joo JaeEun,
Ham WonHun
Publication year - 2012
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.201200065
Subject(s) - pyrrolidine , chemistry , piperidine , stereoselectivity , intramolecular force , ring closing metathesis , metathesis , ketone , stereochemistry , hydride , alkaloid , alcohol , organic chemistry , polymerization , metal , polymer , catalysis
Concise stereoselective syntheses of (+)‐α‐conhydrine and its pyrrolidine analogue are described. The key features are a highly diastereoselective chelation‐controlled hydride reduction of the amino ketone, to give the anti amino alcohol directly, and an intramolecular ring‐closing metathesis.