Abstract
AbstractA divergent procedure for nucleophilic ring‐opening of vinyl epoxides with alkynes has been developed. The combination of lithium acetylides and BF3·OEt2 afforded the SN2 products, whereas alkynylalanes gave SN2′ 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 be rearranged into γ‐butyrolactones. The synthetic utility of the process is demonstrated by a short synthesis of γ‐butyrolactone 24, a key intermediate in the synthesis of prostaglandin PGF2α. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
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