Journal
HETEROCYCLES
Volume 80, Issue 2, Pages 1463-1469Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-09-S(S)95
Keywords
Cyclization; Palladium Catalyzed Reaction; Cross Metathesis; 1,3-Chirality Transfer; Oxa- and Aza-Heterocycles
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
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A concise synthesis of chiral non-racemic 2-(3-benzoyloxyprop-1-enyl)tetrahydrofuran (5a), tetrahydropyran (5b), and piperidine (8) is described. Cross-metathesis of optically pure (S)-1-O-benzoyl-3-butene-1,2-diol (2) with protected 4-pentenol, 5-hexenol, and 5-hexenylamine gave the corresponding ally! alcohols (3a), (3b), and (7) in one step, respectively. PdCl(2)(MeCN)(2) catalyzed cyclization of 4a, 4b, and 7 afforded 5a, 5b, and 8 in excellent yields with high enantiomeric purity.
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