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Regioselective and ...
Abstract
Ämnesord
Stäng
- 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).
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- vinyl epoxides
- epoxide opening
- alkyne nucleophiles
- regioselectivity
- Organic chemistry
- Organisk kemi
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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