Base-Mediated Ring-Opening Reactions of Episulfones to give Alkenylsulfinates: A Stereoselective Synthesis of Alkenyl Sulfones

Synlett

Volumn 1996, Issue 1, 1996, Pages 27-28

  Dishington, Allan P ^a   Muccioli, Adriano B ^a   Simpkins, Nigel S ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542715594     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5322     Document Type: Article

References (11)

1. Muccioli, A. B.; Simpkins, N. S.; Mortlock, A. J. Org. Chem. 1994, 59, 5141. See also Graham, A. E.; Loughlin, W. A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 7281.
2. Muccioli, A. B.; Simpkins, N. S.; Mortlock, A. J. Org. Chem. 1994, 59, 5141. See also Graham, A. E.; Loughlin, W. A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 7281.
3. See Refvik, M. D.; Froese, R. D. J.; Goddard, J. D.; Pham, H. H.; Pippert, M. F.; Schwan, A. L. J. Am. Chem. Soc. 1995, 117, 184, and references therein.
4. Matsumura, S.; Nagai, T.; Tokura, N. Bull. Chem. Soc. Jpn. 1968, 41, 2672. Jarvis, B. B.; Tong, W. P.; Ammon, H. L. J. Org. Chem. 1975, 40, 3189.
5. Matsumura, S.; Nagai, T.; Tokura, N. Bull. Chem. Soc. Jpn. 1968, 41, 2672. Jarvis, B. B.; Tong, W. P.; Ammon, H. L. J. Org. Chem. 1975, 40, 3189.
6. For a review of sulfone preparation by sulfmate alkylation, see Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press Ltd. 1993, Chapter 2.
7. 1H NMR spectrum shows a characteristic downfield shift in the (E) isomer (δ ca. 6.7) compared with the (Z)-isomer (δ ca. 6.2).
8. For previous access to alkenyl sulfinates, see Palmer, J. T.; Fuchs, P. L. Synth. Commun. 1988, 233.
9. (a) Opitz, G.; Rieth, K.; Ehlis, T. Chem. Ber. 1990, 123, 1563 and 1989.
10. (b) Opitz, G.; Ehlis, T.; Rieth, K. Tetrahedron Lett. 1989, 30, 3131.
11. (c) For a review, see Fischer, N. H. Synthesis 1970, 393.