Highly Stereoselective Synthesis of cis-2-Substituted-3-vinyltetrahydrofurans from (Z)-Trimethyl(5-trimethylsiloxy-2-pentenyl)silane and Acetals

Synlett

Volumn 1997, Issue 6, 1997, Pages 716-718

  Sano, Tomohumi ^a   Oriyama, Takeshi ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003453771     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3261     Document Type: Article

References (11)

1. Mekhalfia, A.; Markó, I. E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. Markó, I. E.; Bayston, D. J.; Mekhalfia, A.; Adams, H. Bull. Soc. Chim. Belg. 1993, 102, 655.
2. Mekhalfia, A.; Markó, I. E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. Markó, I. E.; Bayston, D. J.; Mekhalfia, A.; Adams, H. Bull. Soc. Chim. Belg. 1993, 102, 655.
3. Mekhalfia, A.; Markó, I. E.; Adams, H. Tetrahedron Lett. 1991, 32, 4783. Markó, I. E.; Mekhalfia, A.; Bayston, D. J.; Adams, H. J. Org. Chem. 1992, 57, 2211. Markó, I. E.; Bayston, D. J.; Mekhalfia, A.; Adams, H. Bull. Soc. Chim. Belg. 1993, 102, 655.
4. Markó, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595.
5. Oriyama, T.; Jshiwata, A.; Sano, T.; Matsuda, T.; Takahashi, M.; Koga, G. Tetrahedron Lett. 1995, 36, 5581.
6. -1 2955, 1250, 1097, 841.
7. The assignment of stereochemistry was determined by the conversion of 2-phenyl-3-vinyltetrahydrofuran into the known compound, cis-3-methyl-2-phenyltetrahydrofuran. Dana, G.; Touboul, E.; Convert, O.; Pascal, Y. L. Tetrahedron, 1988, 44, 429.
8. -1 2873, 1639, 1493, 1063, 914, 724. Chemical shift of vinylic methine proton of trans-isomer showed lower field (S 5.82) which corresponded to δ 5.26 of cis-isomer.
9. 2.
10. 3/MeOH), and 3) trimethylsilylation (TMSCl / imidazole).
11. Mohr, P. Tetrahedron Lett. 1993, 34, 6251.