Enantioselective syntheses of organosulfur compounds via [2,3] sigmatropic rearrangements of ylides derived from di(allyl), di(propargyl), and di(benzyl) sulfide complexes; control of carbon configuration by an easily resolved and recycled rhenium auxiliary

Pure and Applied Chemistry

Volumn 68, Issue 1, 1996, Pages 79-88

  Meyer, Oliver ^a   Cagle, Phillip C ^a   Weickhardt, Konrad ^a   Vichard, Dominique ^a   Gladysz, J A ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001893022     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668010079     Document Type: Article

References (30)

1. (a) I.E. Markó, in Comprehensive Organic Synthesis; B.M. Trost, Editor-in-Chief; I. Fleming, Deputy Editor-in-Chief; G. Pattenden, Volume Editor, Vol 3, Chapter 3.10, Pergamon, New York (1991).
2. (b) E. Vedejs. Acc. Chem. Res. 17, 358 (1984).
3. (a) B.M. Trost and R.F. Hammen. J. Am. Chem. Soc. 95, 962 (1973).
4. (b) B.M. Trost and W.G. Biddlecom. J. Org. Chem. 38, 3438 (1973).
5. (a) P.C. Cagle, A.M. Arif and J.A. Gladysz. J. Am. Chem. Soc. 116, 3655 (1994).
6. (b) P.C. Cagle, O. Meyer, K. Weickhardt, A.M. Arif and J.A. Gladysz. J. Am. Chem. Soc. in press.
7. J.H. Merrifield, J.M. Fernández, W.E. Buhro and J.A. Gladysz. Inorg. Chem. 23, 4022 (1984).
8. J.J. Kowalczyk, S.K. Agbossou and J.A. Gladysz. J. Organomet. Chem. 397, 333 (1990).
9. The configuration at rhenium is specified first (and according to conventions described previously) (5), followed by those of any SCC (Cα) and SCC (Cβ) stereocenters.
10. N. Quirós Méndez, A.M. Arif and J.A. Gladysz. Organometallics 10, 2199 (1991).
11. K.K. Anderson, in The Chemistry of the Sulphonium Group; C.J.M. Stirling and S. Patai, Eds.; Chapter 10, Wiley, New York (1981).
12. M.A. Dewey, Y. Zhou, Y. Liu and J.A. Gladysz. Organometallics 12, 3924 (1993).
13. (a) W.A. Schenk, J. Frisch, W. Adam and F. Prechtl. Inorg. Chem. 31, 3329 (1992).
14. (b) W. Henderson, B.K. Nicholson and R.D.W. Kemmitt. J. Chem. Soc., Dalton Trans. 2489 (1994).
15. (a) J.M. Fernández and J.A. Gladysz. Organometallics 8, 207 (1989).
16. (b) M.A. Dewey, D.A. Knight, D.P. Klein, A.M. Arif and J.A. Gladysz. Inorg. Chem. 30, 4995 (1991).
17. G.B. Richter-Addo, D.A. Knight, M.A. Dewey, A.M. Arif and J.A. Gladysz. J. Am. Chem. Soc. 115, 11863 (1993).
18. (a) G.L. Crocco, K.E. Lee and J.A. Gladysz. Organometallics 9, 2819 (1990).
19. (b) S.G. Davies, I.M. Dordor-Hedgecock, K.H. Sutton and M. Whittaker. J. Am. Chem. Soc. 109, 5711 (1987).
20. (c) S.C. Mackie and M.C. Baird. Organometallics 11, 3712 (1992).
21. - have an allyl group in this region (Fig. 1, left; Fig. 2, left). This constitutes the first time (out of numerous opportunities) that an adduct of I and a Lewis base with a hydrogen or lone pair on the ligating atom has crystallized without the hydrogen or lone pair in this position (7,11b,13a,15).
22. J.I. Seeman. Chem. Rev. 83, 83 (1983).
23. One rationale for the lower diastereoselectivities with the stronger bases in TABLE 2 would be lower deprotonation selectivities. However, if as we propose the Curtin-Hammett limit applies, interactions between 6 and the various conjugate acids may be invoked. An obvious possibility would be hydrogen bonding, which has been observed with amine (11b) and phosphine (21) adducts of I.
24. (a) H. Brunner. Angew. Chem., Int. Ed. Engl. 22, 897 (1983); see sections 6-8.
25. (b) R. Hunter, R.H. Haueisen and A. Irving. Angew. Chem., Int. Ed. Engl. 33, 566 (1994), and references therein,
26. (c) I. Dance and M. Scudder. J. Chem. Soc., Chem. Commun. 1039 (1995).
27. Y.D. Wu and K.N. Houk. J. Org. Chem. 56, 5657 (1991), and references therein.
28. P.C. Cagle, O. Meyer, D. Vichard, K. Weickhardt, A.M. Arif and J.A. Gladysz. submitted to Organometallics.
29. P.C. Cagle, P.T. Bell and J.A. Gladysz. manuscript in preparation.
30. B.D. Zwick, M.A. Dewey, D.A. Knight, W.E. Buhro, A.M. Arif and J.A. Gladysz. Organometallics 11, 2673 (1992).