Palladium-catalyzed carbonylation of 2-(propargyl)allyl phosphates leading to highly unsaturated γ-lactones

Angewandte Chemie - International Edition

Volumn 42, Issue 12, 2003, Pages 1397-1399

  Kamitani, Akihito ^a   Chatani, Naoto ^a   Mitrai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbonylation; Cyclization; Homogeneous catalysis; Lactones; Palladium

Indexed keywords

CARBONYLATION; CATALYSIS; PALLADIUM; REACTION KINETICS;

MILD REACTION CONDITIONS;

PHOSPHATES;

CARBON MONOXIDE; LACTONE DERIVATIVE; PALLADIUM; PHOSPHATE; UNSATURATED FATTY ACID;

AMBIENT AIR; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CARBONYLATION; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; INFRARED RADIATION; PRESSURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037471216     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390359     Document Type: Article

References (25)

1. E. Negishi, M. Kotora, Tetrahedron 1997, 53, 6707.
2. Y. S. Rao, Chem. Rev. 1976, 76, 625; S. V. Ley, L. R. Cox, G. Meek, Chem. Rev. 1996, 96, 423; I. Collins, J. Chem. Soc. Perkin Trans. 1 1998, 1869; I. Collins, J. Chem. Soc. Perkin Trans. 1 1999, 1377.
3. Y. S. Rao, Chem. Rev. 1976, 76, 625; S. V. Ley, L. R. Cox, G. Meek, Chem. Rev. 1996, 96, 423; I. Collins, J. Chem. Soc. Perkin Trans. 1 1998, 1869; I. Collins, J. Chem. Soc. Perkin Trans. 1 1999, 1377.
4. Y. S. Rao, Chem. Rev. 1976, 76, 625; S. V. Ley, L. R. Cox, G. Meek, Chem. Rev. 1996, 96, 423; I. Collins, J. Chem. Soc. Perkin Trans. 1 1998, 1869; I. Collins, J. Chem. Soc. Perkin Trans. 1 1999, 1377.
5. Y. S. Rao, Chem. Rev. 1976, 76, 625; S. V. Ley, L. R. Cox, G. Meek, Chem. Rev. 1996, 96, 423; I. Collins, J. Chem. Soc. Perkin Trans. 1 1998, 1869; I. Collins, J. Chem. Soc. Perkin Trans. 1 1999, 1377.
6. N. Chatani, T Morimoto, Y. Fukumoto, S. Mural, J. Am. Chem. Soc. 1998, 120, 5335.
7. N. Chatani, M. Tobisu, T. Asaumi, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1999,121, 7160; M. Tobisu, N. Chatani, T. Asaumi, K. Amako, Y. Ie, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 2000, 122, 12663.
8. N. Chatani, M. Tobisu, T. Asaumi, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 1999,121, 7160; M. Tobisu, N. Chatani, T. Asaumi, K. Amako, Y. Ie, Y. Fukumoto, S. Murai, J. Am. Chem. Soc. 2000, 122, 12663.
9. For applications to the construction of lactams, see: N. Chatani, T. Morimoto, A. Kamitani, Y. Fukumot, S. Murai, J. Organomet. Chem. 1999, 579, 177; N. Chatani, M. Tobisu, T. Asaumi, S. Murai, Synthesis 2000, 925; A. Göbel, W. Imhof, Chem. Commun. 2001, 593.
10. For applications to the construction of lactams, see: N. Chatani, T. Morimoto, A. Kamitani, Y. Fukumot, S. Murai, J. Organomet. Chem. 1999, 579, 177; N. Chatani, M. Tobisu, T. Asaumi, S. Murai, Synthesis 2000, 925; A. Göbel, W. Imhof, Chem. Commun. 2001, 593.
11. For applications to the construction of lactams, see: N. Chatani, T. Morimoto, A. Kamitani, Y. Fukumot, S. Murai, J. Organomet. Chem. 1999, 579, 177; N. Chatani, M. Tobisu, T. Asaumi, S. Murai, Synthesis 2000, 925; A. Göbel, W. Imhof, Chem. Commun. 2001, 593.
12. 5 resulted in a [2+2+1] cyclo-addition, leading to cyclopentediones, in which the ketene carbonyl group had not been incorporated. K. Kinugawa, T. Agawa, Organomet. Chem. Synth. 1972, 1, 427.
13. T. T. Tidwell, Ketenes, Wiley, New York, 1995; T. T. Tidwell, Acc. Chem. Res. 1990, 23, 273.
14. T. T. Tidwell, Ketenes, Wiley, New York, 1995; T. T. Tidwell, Acc. Chem. Res. 1990, 23, 273.
15. S. Torii, H. Okumoto, M. Sadakane, A. K. M. A. Hai, H. Tanaka, Tetrahedron Lett. 1993, 34, 6553; H. Tanaka, A. K. M. A. Hai, M. Sadakane, H. Okumoto, S. Torii, J. Org. Chem. 1994, 59, 3040. See also: Z. Zhou, H. Alper, J. Org. Chem. 1996, 61, 1256; C. S. Cho, J. C. Park, L. H. Jiang, T.-J. Kim, S. C. Shim, M. C. Kim, Bull. Korean Chem. Soc. 2000, 21, 541.
16. S. Torii, H. Okumoto, M. Sadakane, A. K. M. A. Hai, H. Tanaka, Tetrahedron Lett. 1993, 34, 6553; H. Tanaka, A. K. M. A. Hai, M. Sadakane, H. Okumoto, S. Torii, J. Org. Chem. 1994, 59, 3040. See also: Z. Zhou, H. Alper, J. Org. Chem. 1996, 61, 1256; C. S. Cho, J. C. Park, L. H. Jiang, T.-J. Kim, S. C. Shim, M. C. Kim, Bull. Korean Chem. Soc. 2000, 21, 541.
17. S. Torii, H. Okumoto, M. Sadakane, A. K. M. A. Hai, H. Tanaka, Tetrahedron Lett. 1993, 34, 6553; H. Tanaka, A. K. M. A. Hai, M. Sadakane, H. Okumoto, S. Torii, J. Org. Chem. 1994, 59, 3040. See also: Z. Zhou, H. Alper, J. Org. Chem. 1996, 61, 1256; C. S. Cho, J. C. Park, L. H. Jiang, T.-J. Kim, S. C. Shim, M. C. Kim, Bull. Korean Chem. Soc. 2000, 21, 541.
18. S. Torii, H. Okumoto, M. Sadakane, A. K. M. A. Hai, H. Tanaka, Tetrahedron Lett. 1993, 34, 6553; H. Tanaka, A. K. M. A. Hai, M. Sadakane, H. Okumoto, S. Torii, J. Org. Chem. 1994, 59, 3040. See also: Z. Zhou, H. Alper, J. Org. Chem. 1996, 61, 1256; C. S. Cho, J. C. Park, L. H. Jiang, T.-J. Kim, S. C. Shim, M. C. Kim, Bull. Korean Chem. Soc. 2000, 21, 541.
19. G. Wu, I. Shimoyama, E. Negishi, J. Org. Chem. 1991, 56, 6506.
20. All new compounds were characterized by NMR, IR, mass spectral data, and by elemental analyses or high-resolution mass spectra. See Supporting Information.
21. We do not know whether CO insertion takes place into a C-Pd bond or a O-Pd bond in complex 6.
22. Related Pd or Rh complexes were proposed. C. Coperet, T. Sugihara, G. Wu, L. Shimoyama, E. Negishi, J. Am. Chem. Soc. 1995, 117, 3422; B. Van den Hoven, B. El Ali, H. Alper, J. Org. Chem. 2000, 65, 4131.
23. Related Pd or Rh complexes were proposed. C. Coperet, T. Sugihara, G. Wu, L. Shimoyama, E. Negishi, J. Am. Chem. Soc. 1995, 117, 3422; B. Van den Hoven, B. El Ali, H. Alper, J. Org. Chem. 2000, 65, 4131.
24. An alternative path, as shown below, also exists. See ref. [9].
25. Negishi et al. reported a new synthesis of polyunsaturated lactones by a carbometalation-carbonylation cascade, which is closely related to our system. T. Sugihara, C. Coperet, Z. Owczarczyk, L. Harring, E. Negishi, J. Am. Chem. Soc. 1994, 116, 7923.