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Synthesis 2002(3): 0393-0398
DOI: 10.1055/s-2002-20041
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Synthesis of 6-Tributylstannyl-3,4-dihydro-2H-pyrans via Coupling of Enol Triflates with (Bu3Sn)(Bu)CuLi·LiCN

Tanya Wildmana, Philip J. Kocienski*a, Robert Narquiziana, William G. Whittinghamb
a Department of Chemistry, Leeds University, Leeds, LS2 9JT, UK
Fax: +44(113)2336401; e-Mail: p.kocienski@chemistry.leeds.ac.uk;
b Syngenta, Jealott"s Hill International Research Station, Bracknell, Berkshire RG42 6EY, UK
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Publication History

Received 2 January 2002
Publication Date:
28 July 2004 (online)

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Abstract

Enol triflates derived from 6- and 7-membered ring lactones (6 cases) react with (Bu3Sn)(Bu)CuLi·LiCN in THF at -78 °C to give the corresponding α-tributylstannyl cyclic enol ethers in 54-85% yield.

Key words

cyanocuprate - coupling - enol triflate - stannane - transmetallation - tin - dihydropyran