Origins of Regio- and Stereoselectivity in Additions of Phenylselenenyl Chloride to Allylic Alcohols and the Applicability of These Additions to a Simple 1,3-Enone Transposition Sequence

Journal of Organic Chemistry

Volumn 47, Issue 7, 1982, Pages 1258-1267

  Liotta, Dennis ^a   Zima, George ^a   Saindane, Manohar ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001632904     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00346a022     Document Type: Article

References (20)

1. Fellow of the Alfred P. Sloan Foundation, 1980–1984. Recipient of a Camille and Henry Dreyfus Teacher-Scholar Fellowship, 1981–1986.
2. For additions of simple selenium electrophiles to double bonds, see: (a) Liotta, D.; Zima, G. Tetrahedron Lett. 1978, 4977.
3. Sharpless, K.B.; Lauer, R.F.J. Org. Chem. 1974, 39, 429.
4. Reich, H.J.J. Org. Chem. (1974) 39, 428.
5. Clive, D.L.J.J. Chem. Soc., Chem. Commun. 1974, 100.
6. Raucher, S.J. Org. Chem. 1977, 42, 2950.
7. Kataev, E.G.; Mannafov, T.G.; Berdnikov, K.A.; Kamarovskaya, O.A. Zh. Org. Khim 1973, 9, 1983.
8. For the use of selenium electrophiles in the confunctionalization of double bonds, see: (a) Clive, D.L.J.; Chittattu, G.J. Chem. Soc., Chem. Commun. 1977, 484.
9. Nicolaou, K.C.; Sertz, S.P.; Sipio, W.J.; Blount, J.F.J. Am. Chem. Soc. 1979, 101, 3884.
10. Liotta, D.; Zima, G.J. Org. Chem. 1980, 45, 2551.
11. Simple episelenonium ions have been observed spectroscopically. See: Schmid, G.H.; Garratt, D.G. Tetrahedron Lett. 1975, 3991.
12. Sharpless has previously shown that selenoxide eliminations preferentially occur away from an oxygen substituent. See: Sharpless, K.B.; Lauer, R.F.J. Am. Chem. Soc. 1973, 95, 2697.
13. For examples of simple and alkylative 1,3-enone transpositions, see: (a) Wharton, P.S.; Bohlen, D.H.J. Org. Chem. 1961, 26, 3615.
14. Wharton, P.S.J. Org. Chem. 1961, 26, 4781.
15. Trost, B.M.; Shanton, J.L.J. Am. Chem. Soc. 1975, 97, 4018.
16. Trost, B.M.; Hiroi, K.; Holy, N.J. Am. Chem. Soc. 1975, 97, 5873.
17. Reich, H.J.; Wollowitz, S.; Trend, J.E.; Chow, F.; Wendelborn, D.F.J. Org. Chem. 1978, 43, 1697.
18. Martin, S.F.; Chow, T. Tetrahedron Lett. 1978, 1943.
19. Martin, S.F., personal communication, University Texas, Austin.
20. Lansbury, P.T. Acc. Chem. Res. 1972, 5, 311.