Efficient access to chiral trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines via allylation of chiral imines and ring-closing metathesis

Enantiomerically pure trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines are synthesized in five steps from Garner's aldehyde in 37–44% overall yield. This strategy is based on the allylation of chiral iminoalcohols formed in situ followed by a ring-closing metathesis. Graphic

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Bibliographic Details
Published inTetrahedron letters Vol. 44; no. 3; pp. 527 - 530
Main Authors Felpin, François-Xavier, Lebreton, Jacques
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.01.2003
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
ORGANOMETALLIC REAGENTS
ENANTIOSELECTIVE SYNTHESIS
AMINO
PIPERIDINES
STEREOSELECTIVE SYNTHESIS
ALKALOIDS
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Summary:Enantiomerically pure trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines are synthesized in five steps from Garner's aldehyde in 37–44% overall yield. This strategy is based on the allylation of chiral iminoalcohols formed in situ followed by a ring-closing metathesis. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)02586-8