Photochemical Initiated Cleavage of Carbon-Sulfur Bond in 1,3-Dithiolane, 1,3-Oxathiolane, 5-Oxo-1,3-oxathiolane, 1,3-Thiazolidine Derivatives and Asymmetric 1,2-Induction with N(Substituted) α-Aminoalkyl Radicals

Synlett

Volumn 1996, Issue 3, 1996, Pages 237-238

  Lesage, Maurice ^a   Arya, Prabhat ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001158096     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5387     Document Type: Article

References (21)

1. Issued as NRCC publication number 39087
2. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds by Giese, B., Pergamon Press, 1986; Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev., 1991, 91, 1237.
3. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds by Giese, B., Pergamon Press, 1986; Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev., 1991, 91, 1237.
4. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds by Giese, B., Pergamon Press, 1986; Giese, B. Angew. Chem. Int. Ed. Engl. 1989, 28, 969; Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev., 1991, 91, 1237.
5. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
6. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
7. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
8. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
9. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
10. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
11. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
12. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
13. Porter, N. A; Giese, B.; Curran, D. P. Acc. Chem. Res., 1991, 24, 296 and references therein; Hart, D. J.; Krishnamurthy, R. Synlett, 1991, 412; Guindon, Y.; Lavallée, J.-F.; Brunet, M. L.; Horner, G.; Rancourt, J. J. Am. Chem. Soc., 1991, 113, 9701; Giese, B.; Bulliard, M.; Zeitz, H.-G. Synlett, 1991, 425; Giese, B.; Damm W.; Dickhaut, J.; Wetterich, F. Tetrahedron Lett., 1991, 32, 6097; Curran, D. P.; Thoma, G. J. Am. Chem. Soc., 1992, 114, 4436; Renaud, P.; Björup, P.; Carrupt, P.-A.; Schenk, K.; Schubert, S. Synlett, 1992, 211; Thoma, G.; Curran, D. P.; Geib, S. V.; Giese, B.; Damm, W.; Wetterich, F. J. Am. Chem. Soc., 1993, 115, 8585; Curran, D. P.; Sun, S. Tetrahedron Lett., 1993, 34, 6181,
14. Arya, P.; Samson, C.; Lesage, M.; Griller, D. J. Org. Chem., 1990, 55, 6248; Arya, P.; Lesage, M.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 2853; Arya, P.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 6265; Yadav, V. K.; Fallis, A. G. Tetrahedron Letts. , 1988, 29, 897 and 1989, 30, 3283;
15. Arya, P.; Samson, C.; Lesage, M.; Griller, D. J. Org. Chem., 1990, 55, 6248; Arya, P.; Lesage, M.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 2853; Arya, P.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 6265; Yadav, V. K.; Fallis, A. G. Tetrahedron Letts. , 1988, 29, 897 and 1989, 30, 3283;
16. Arya, P.; Samson, C.; Lesage, M.; Griller, D. J. Org. Chem., 1990, 55, 6248; Arya, P.; Lesage, M.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 2853; Arya, P.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 6265; Yadav, V. K.; Fallis, A. G. Tetrahedron Letts. , 1988, 29, 897 and 1989, 30, 3283;
17. Arya, P.; Samson, C.; Lesage, M.; Griller, D. J. Org. Chem., 1990, 55, 6248; Arya, P.; Lesage, M.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 2853; Arya, P.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 6265; Yadav, V. K.; Fallis, A. G. Tetrahedron Letts. , 1988, 29, 897 and 1989, 30, 3283;
18. Arya, P.; Samson, C.; Lesage, M.; Griller, D. J. Org. Chem., 1990, 55, 6248; Arya, P.; Lesage, M.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 2853; Arya, P.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 6265; Yadav, V. K.; Fallis, A. G. Tetrahedron Letts. , 1988, 29, 897 and 1989, 30, 3283;
19. (b) Fallis, A. G.; Yadav, V. K. Can. J. Chem., 1991, 69, 779.
20. With examples 12 and 13, intramolecular cyclization to form the carbon-carbon bond has been obtained under thermal reaction conditions (Arya, P.; Wayner, D. D. M. Tetrahedron Lett., 1991, 32, 6265). 12a and 12b, 13a and 13b were found to be diastereomers by GC-MS analysis.
21. 1H NMR (600MHz) 7.33 (s, 5H), 5.1 (s, 2H), 4.10 (m, 4H), 3.46 (dq, J 6.6& 10.6Hz, 1H), 2.63 (m, 2H), 1.9 (m, 2H), 1.74 (m, 2H), 1.59 (m ,1H), 1.0 (d, J 6.5Hz, 3H).