Ru- and Rh-catalyzed C-C bond cleavage of cyclobutenones: Reconstructive and selective synthesis of 2-pyranones, cyclopentenes, and cyclohexenones

Angewandte Chemie - International Edition

Volumn 43, Issue 40, 2004, Pages 5369-5372

  Kondo, Teruyuki ^a   Taguchi, Yoshinori ^a   Kaneko, Yushi ^a   Niimi, Masatsugu ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

C C activation; Homogeneous catalysis; Metallacycles; Rhodium; Ruthenium

Indexed keywords

BUTENES; CHEMICAL BONDS; DIMERIZATION; RHODIUM; RUTHENIUM;

COUPLING REACTIONS; RING OPENING DIMERIZATION;

CATALYSIS;

2 CYCLOHEXENONE DERIVATIVE; 2 PYRONE DERIVATIVE; ALKENE DERIVATIVE; ARGON; CARBON; CYCLOBUTANONE DERIVATIVE; CYCLOHEPTENE; CYCLOPENTENE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; NORBORNENE DERIVATIVE; RHENIUM; RHODIUM COMPLEX; RUTHENIUM;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIELS ALDER REACTION; DIMERIZATION; DISSOCIATION; ELIMINATION REACTION; ISOMERIZATION; OXIDATION; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; RING OPENING; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 7244245518     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461002     Document Type: Article

References (24)

1. For reviews, see: a) K. C. Bishop III, Chem. Rev. 1976, 76, 461-486;
2. b) R. H. Crabtree, Chem. Rev. 1985, 85, 245-269;
3. c) P. W. Jennings, L. L. Johnson, Chem. Rev. 1994, 94, 2241-2290;
4. d) M. Murakami, Y. Ito in Activation of Unreactive Bonds and Organic Synthesis (Ed.: S. Murai), Springer, New York, 1999, pp. 97-129;
5. e) T. Mitsudo, T. Kondo, Synlett 2001, 309-321.
6. For green chemistry, see: a) P. T. Anatas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694;
7. b) B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
8. T. Kondo, A. Nakamura, T. Okada, N. Suzuki, K. Wada, T. Mitsudo, J. Am. Chem. Soc. 2000, 122, 6319-6320.
9. T. Kondo, Y. Kaneko, Y. Taguchi, A. Nakamura, T. Okada, M. Shiotsuki, Y. Ura, K. Wada, T. Mitsudo, J. Am. Chem. Soc. 2002, 124, 6824-6825.
10. For reviews, see: a) H. W. Moore, B. R. Yerxa in Advances in Strain in Organic Chemistry, Vol. 4 (Ed.: B. Halton), JAI, London, 1995, pp. 81-162;
11. b) T. K. M. Shing, Methods of Organic Chemistry (Houben-Weyl) 4th ed. 1952-, Vol. E17f (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, chap. 8B, pp. 898-913.
12. a) M. A. Huffman, L. S. Liebeskind, W. T. Pennington, Jr., Organometallics 1990, 9, 2194-2196;
13. b) M. A. Huffman, L. S. Liebeskind, J. Am. Chem. Soc. 1990, 112, 8617-8618;
14. c) M. A. Huffman, L. S. Liebeskind, J. Am. Chem. Soc. 1991, 113, 2771-2772;
15. d) M. A. Huffman, L. S. Liebeskind, W. T. Pennington, Organometallics 1992, 11, 255-266.
16. A thermal reaction of cyclobutenones with activated alkynes to phenols via a vinylketene intermediate has also been reported. a) R. L. Danheiser, S. K. Gee, J. Org. Chem. 1984, 49, 1672-1674;
17. b) R. L. Danheiser, A. Nishida, S. Savariar, M. P. Trova, Tetrahedron Lett. 1988, 29, 4917-4920.
18. a) M. F. Semmelhack, R. Tamura, W. Schnatter, J. Park, M. Steigerwald, S. Ho, Stud. Org. Chem. 1986, 25, 21-42;
19. b) S. E. Gibson, M. A. Peplow, Adv. Organomet. Chem. 1999, 44, 275-355, and references therein.
20. S. A. Benyunes, S. E. Gibson, M. A. Peplow, Chem. Commun. 1996, 1757-1758.
21. Although it is not yet clear why the stereochemistry of 2 changed depending on the catalyst used, we now believe that the present isomerization reaction of diene 7 to 2-pyranone 2 may proceed through addition-elimination of a H-[M] species to 1,3-dienes 7, generating π-allylmetal intermediates such as A and B. A π- (diagram pesented) allylrhodium intermediate has an energetically favorable syntype configuration (A) leading to the selective formation of (E)-2, while a sterically congested anti-type π-allylruthenium species (B), which is also postulated as a key intermediate in our previously reported ruthenium-catalyzed codimerization of 1,3-dienes with acrylic compounds, could be generated to give (Z)-2 in good selectivity. See: T. Mitsudo, S.-W. Zhang, T. Kondo, Y. Watanabe, Tetrahedron Lett. 1992, 33, 341-344.
22. S. Inagaki, H. Fujimoto, K. Fukui, J. Am. Chem. Soc. 1976, 98, 4054-4061.
23. a) R. L. Danheiser, S. Savariar, D. D. Cha, Org. Synth. 1990, 68, 32-40;
24. b) A. A. Ammann, M. Rey, A. S. Dreiding, Helv. Chim. Acta 1987, 70, 321-328.