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Diastereoselective Synthesis of 2,6‐ trans ‐Disubstituted Piperidines via Sequential Cross‐Metathesis–Cationic Cyclisation
Author(s) -
Mix Stefan,
Blechert Siegfried
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600482
Subject(s) - enantiopure drug , chemistry , piperidine , metathesis , ruthenium , allylic rearrangement , cationic polymerization , indolizidine , salt metathesis reaction , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , alkaloid , polymer , polymerization
Abstract Ruthenium‐catalysed cross‐metathesis of protected homoallylamine derivatives with vinyl carbinols furnished allylic alcohols, which underwent stereoconvergent cyclisation to trans ‐tetrahydropyridines upon treatment with BF 3 ⋅OEt 2 . The new methodology was used for the preparation of enantiopure piperidine and indolizidine natural products.