Diastereoselective Synthesis of 2,6‐ trans ‐Disubstituted Piperidines  via  Sequential Cross‐Metathesis–Cationic Cyclisation | Zendy

Mix Stefan | Zendy; Blechert Siegfried | Zendy

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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

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.

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