Platinum(0)-catalyzed carbonylative lactonization of 5-hydroxy-1-pentyne with carbon monoxide in the presence of thiols

Organometallics

Volumn 17, Issue 14, 1998, Pages 3111-3114

  Ogawa, Akiya ^a   Kawabe, Ken Ichi ^a   Kawakami, Jun Ichi ^a   Mihara, Masatoshi ^a   Hirao, Toshikazu ^a   Sonoda, Noboru ^b  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001449823     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9801857     Document Type: Article

References (17)

1. Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991; pp 173-189.
2. (a) Murray, T. F.; Samsel, E. G.; Varma, V.; Norton, J. R. J. Am. Chem. Soc. 1981, 103, 7520.
3. (b) Murray, T. F.; Norton, J. R. J. Am. Chem. Soc. 1979, 101, 4107.
4. (c) Murray, T. F.; Varma, V.; Norton, J. R. J. Org. Chem. 1978, 43, 353.
5. (d) Murray, T. F.; Varma, V.; Norton, J. R. J. Am. Chem. Soc. 1977, 99, 8085.
6. (e) Norton, J. R.; Shenton, K. E.; Schwartz, J. Tetrahedron Lett. 1975, 51.
7. (f) Tsuji, Y.; Kondo, T.; Watanabe, Y. J. Mol. Catal. 1987, 40, 295.
8. Ogawa, A.; Kawakami, J.; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380.
9. The other explanation is suggested to involve the formation of an acylplatinum intermediate (5b), followed by cyclization of 5b to the δ-lactone (2b). (Matrix Presented)
10. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
11. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
12. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
13. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
14. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
15. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
16. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.
17. For the synthesis of α-methylene-δ-lactone (2b), see: (a) Paterson, I. Tetrahedron 1988, 44, 4207. (b) Murray, A. W.; Reid, R. G. J. Chem. Soc., Chem. Commun. 1984, 132. (c) Mori, M.; Washioka, Y.; Urayama, T.; Yoshiura, K.; Chiba, K.; Ban, Y. J. Org. Chem. 1983, 48, 4058. (d) Semmelhack, M. F.; Brickner, S. J. J. Org. Chem. 1981, 46, 1723. (e) Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993. (f) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (g) Harmon, A. D.; Hutchinson, C. R. J. Org. Chem. 1975, 40, 3474. (h) Harmon, A. D.; Hutchinson, C. R. Tetrahedron Lett. 1973, 1293.