Regioselective and Divergent Opening of Vinyl Epoxides with Alkyne Nucleophiles
2005 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 18, 3946-3951 p.Article in journal (Refereed) Published
A divergent procedure for nucleophilic ring-opening of vinyl epoxides with alkynes has been developed, The combination of lithium acetylides and BF(3)center dot OEt2 afforded the S(N)2 products, whereas alkynylalanes gave S(N)2' addition. The regioselectivity of these processes is affected by the alkyne substituent. Ethoxyacetylene added with complete regiocontrol under both SN2 and SN2' conditions, and the SN2 isomeric adducts could he rearranged into gamma-butyrolactones. The synthetic utility of the process is demonstrated by a short synthesis of gamma-butyrolactone 24, a key intermediate in the synthesis of prostaglandin PGF(20).
Place, publisher, year, edition, pages
2005. Vol. 18, 3946-3951 p.
vinyl epoxides, epoxide opening, alkyne nucleophiles, regioselectivity
IdentifiersURN: urn:nbn:se:kth:diva-6624DOI: 10.1002/ejoc.200500321ISI: 000232068100010ScopusID: 2-s2.0-24944439877OAI: oai:DiVA.org:kth-6624DiVA: diva2:11382
QC 201009172006-12-152006-12-152010-09-17Bibliographically approved