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

Tanya Wildman; Philip J. Kocienski; Robert Narquizian; William G. Whittingham

doi:10.1055/s-2002-20041

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

Tanya Wildman^a, Philip J. Kocienski*^a, Robert Narquizian^a, William G. Whittingham^b
^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

Abstract

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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

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References

1 Kocienski P. Narquizian R. Raubo P. Smith C. Farrugia LJ. Muir K. Boyle FT. J. Chem. Soc., Perkin Trans. 1 2000, 2357

2 Barber C. Jarowicki K. Kocienski P. Synlett 1991, 197

3 Chong JM. Nielsen N. Tetrahedron Lett. 1998, 39: 9617

4 Lipshutz BH. Ellsworth EL. Dimock SH. Reuter DC. Tetrahedron Lett. 1989, 30: 2065

5 Piers E. Morton HE. Chong JM. Can. J. Chem. 1987, 65: 78

6 Gilbertson SR. Challener CA. Bos ME. Wulff WD. Tetrahedron Lett. 1988, 29: 4795

7 Boeckman RK. Bruza KJ. Tetrahedron 1981, 37: 3997

8 Genicot C. Ley SV. Synthesis 1994, 1275

9 Bailey DM. Johnson RE. J. Org. Chem. 1970, 35: 3574

10 Tokoroyama T. Kusaka H. Can. J. Chem. 1996, 74: 2487

11 Freudenberg K. Schuhmacher G. Chem. Ber. 1954, 87: 1882

12 Stevenson R. Block E. J. Org. Chem. 1971, 36: 3453

13 Noguchi K. Takeda M. Nurimoto S. Chem. Pharm. Bull. 1977, 25: 890

14 Caubere P. Guillaumet G. Mourad MS. Tetrahedron 1972, 28: 95