Alkynol endo-cycloisomerizations and conceptually related transformations

Chemistry - A European Journal

Volumn 5, Issue 11, 1999, Pages 3103-3106

  McDonald, Frank E ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Carbene complexes; Cyclizations; Nucleosides; Oligosaccharides; Synthetic methods

Indexed keywords

ALCOHOL; ALKYNE DERIVATIVE; CARBON; ETHER DERIVATIVE; NITROGEN; NUCLEOSIDE; SULFUR; VINYL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CYCLIZATION; ISOMERISM; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032755406     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991105)5:11<3103::AID-CHEM3103>3.0.CO;2-N     Document Type: Short Survey

References (36)

1. One example of an endo-selective alkynol cycloisomerization was previously reported: M. Riediker, J. Schwartz, J. Am. Chem. Soc. 1982, 104, 5842. These authors reported endo-cyclization for a substrate with alkyne and hydroxyl substituents trans-1,2-disubstituted onto a cyclopentane ring, so that the exocyclization mode was disfavored by ring strain relative to the endocyclic product.
2. An excellent series of comprehensive reviews has been published: a) M. I. Bruce, A. G. Swincer, Adv. Organomet. Chem. 1983, 22, 59;
3. b) M. I. Bruce, Chem. Rev. 1991, 91, 197;
4. c) M. I. Bruce, Chem. Rev. 1998, 98, 2797.
5. M. H. Chisholm, H. C. Clark, J. Am. Chem. Soc. 1972, 94, 1532.
6. M. I. Bruce, A. G. Swincer, B. J. Thomson, R. C. Wallis, Aust. J. Chem. 1980, 33, 2605.
7. C. Bianchini, A. Marchi, N. Mantovani, L. Marvelli, D. Masi, M. Peruzzini, R. Rossi, Eur. J. Inorg. Chem. 1998, 211.
8. For formation of cyclic Group VI oxacarbenes from alkynyl alcohols, see: a) A. Parlier, H. Rudler, J. Chem. Soc. Chem. Commun. 1986, 514;
9. b) K. H. Dötz, W. Sturm, H. G. Alt, Organometallics 1987, 6, 1424;
10. c) P. Quayle, S. Rahman, E. L. M. Ward, J. Herbert, Tetrahedron Lett. 1994, 35, 3801;
11. d) B. Schmidt, P. Kocienski, G. Reid, Tetrahedron 1996, 52, 1617.
12. For studies on structures of group VI metal carbene anions, see: a) C. P. Casey, R. L. Anderson, J. Am. Chem. Soc. 1974, 96, 1230;
13. b) P. Veya, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Organometallics 1994, 13, 214.
14. a) E. O. Fischer, D. Plabst, Chem. Ber. 1974, 107, 3326;
15. b) C. P. Casey, R. L. Anderson, J. Chem. Soc. Chem. Commun. 1975, 895;
16. c) C. F. Bernasconi, Chem. Soc. Rev. 1997, 26, 299.
17. a) F. E. McDonald, C. B. Connolly, M. M. Gleason, T. B. Towne, K. D. Treiber, J. Org. Chem. 1993, 58, 6952;
18. b) F. E. McDonald, C. C. Schultz, J. Am. Chem. Soc. 1994, 116, 9363.
19. F. E. McDonald, C. C. Schultz, A. K. Chatterjee, Organometallics 1995, 14, 3628.
20. F. E. McDonald, J. L. Bowman, Tetrahedron Lett. 1996, 37, 4675.
21. a) F. E. McDonald, M. M. Gleason, J. Am. Chem. Soc. 1996, 118, 6648;
22. b) F. E. McDonald, H. Y. H. Zhu, Tetrahedron 1997, 53, 11061.
23. M. Stieff, S. K. Landis, F. E. McDonald, unpublished results.
24. F. E. McDonald, A. K. Chatterjee, Tetrahedron Lett. 1997, 38, 7687.
25. C. A. Merlic, M. E. Pauly, J. Am. Chem. Soc. 1996, 118, 11 319.
26. F. E. McDonald, T. C. Olson, Tetrahedron Lett. 1997, 38, 7691.
27. J. L. Bowman, F. E. McDonald, unpublished results.
28. a) K. Maeyama, N. Iwasawa, J. Am. Chem. Soc. 1998, 120, 1928;
29. b) K. Maeyama, N. Iwasawa, J. Org. Chem. 1999, 64, 1344.
30. L. G. Huffman, F. E. McDonald, S. Burova, unpublished results.
31. F. E. McDonald, M. M. Gleason, Angew. Chem. 1995, 107, 356; Angew. Chem. Int. Ed. Engl. 1995, 34, 350.
32. F. E. McDonald, M. M. Gleason, Angew. Chem. 1995, 107, 356; Angew. Chem. Int. Ed. Engl. 1995, 34, 350.
33. J. L. Bowman, F. E. McDonald, J. Org. Chem. 1998, 63, 3680.
34. J. D. Rainier, S. P. Allwein, J. Org. Chem. 1998, 63, 5310.
35. F. E. McDonald, H. Y. H. Zhu, J. Am. Chem. Soc. 1998, 120, 4246.
36. Note in proof: A high-yield, tungsten-catalyzed cycloisomerization procedure for dihydropyran synthesis has been recently developed in our laboratory: K. S. Reddy, F. E. McDonald, unpublished results.