Z-Selective intramolecular Horner–Wadsworth–Emmons reaction for the synthesis of macrocyclic alkenes

The Z-selective intramolecular Horner–Wadsworth–Emmons reaction of the substrates (Ar = Ph or o- tBuC 6H 4) gives the 13–18-membered cyclic alkenes selectively (up to Z: E = 97:3) in good yields using NaH in THF under high dilution conditions. The Z-selective intramolecular Horner–Wadsworth–Emmons r...

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Bibliographic Details
Published in:Tetrahedron letters 2011-03, Vol.52 (12), p.1284-1287
Main Authors: Ando, Kaori, Sato, Kaori
Format: Article
Language:English
Subjects:
Alkenes
Chemistry
Dilution
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Macrocyclic compounds
Organic chemistry
Preparations and properties
Synthesis (chemistry)
Tetrahedrons
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Summary:The Z-selective intramolecular Horner–Wadsworth–Emmons reaction of the substrates (Ar = Ph or o- tBuC 6H 4) gives the 13–18-membered cyclic alkenes selectively (up to Z: E = 97:3) in good yields using NaH in THF under high dilution conditions. The Z-selective intramolecular Horner–Wadsworth–Emmons reaction of the substrates 7– 12 (RO) 2P(O)CHR′CO 2Et (R′ = (CH 2) n CHO) (R = Ph or o- tBuC 6H 4) gives the 13–18-membered cyclic alkenes selectively (up to Z: E = 97:3) in good yields using NaH in THF under high dilution conditions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.01.043