Asymmetric catalytic Pauson-Khand reactions with chiral phosphine ligands: Dramatic effects of substituents in 1,6-enyne systems

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 891-895

  Hiroi, Kunio ^a   Watanabe, Takashi ^a   Kawagishi, Ryoko ^a   Abe, Ikuko ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; COBALT; CYCLOPENTENONE DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034606977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02141-3     Document Type: Article

References (20)

1. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
2. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993; Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1994.
3. Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y; Liu, F. Chem. Rev. 1996, 96, 365.
4. Hiroi, K.; Arinaga, Y Tetrahedron Lett. 1994, 35, 153.
5. Hiroi, K.; Arinaga, Y.; Ogino, T. Chem. Pharm. Bull. 1994, 42, 470.
6. Hiroi, K.; Yoshida, Y.; Kaneko, Y. Tetrahedron Lett. 1999, 40, 3431.
7. Hiroi, K.; Hirasawa, K. Chem. Pharm. Bull. 1994, 42, 786; ibid. 1994, 42, 1036.
8. Hiroi, K.; Hirasawa, K. Chem. Pharm. Bull. 1994, 42, 786; ibid. 1994, 42, 1036.
9. Hiroi, K.; Nakaichi, S.; Minakata, H.; Adachi, J. to be published.
10. For asymmetric Pauson-Khand reactions, see: (a) Shore, N. E. Chem. Rev. 1988, 88, 1081; (b) Shore, N. E. Org. React. 1991, 40, 1; (c) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911; (d) Ingate, S. T.; Marco-Contelles, J. Org. Prep. Proced. Int. 1998, 30, 121, and references cited therein.
11. For asymmetric Pauson-Khand reactions, see: (a) Shore, N. E. Chem. Rev. 1988, 88, 1081; (b) Shore, N. E. Org. React. 1991, 40, 1; (c) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911; (d) Ingate, S. T.; Marco-Contelles, J. Org. Prep. Proced. Int. 1998, 30, 121, and references cited therein.
12. For asymmetric Pauson-Khand reactions, see: (a) Shore, N. E. Chem. Rev. 1988, 88, 1081; (b) Shore, N. E. Org. React. 1991, 40, 1; (c) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911; (d) Ingate, S. T.; Marco-Contelles, J. Org. Prep. Proced. Int. 1998, 30, 121, and references cited therein.
13. For asymmetric Pauson-Khand reactions, see: (a) Shore, N. E. Chem. Rev. 1988, 88, 1081; (b) Shore, N. E. Org. React. 1991, 40, 1; (c) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911; (d) Ingate, S. T.; Marco-Contelles, J. Org. Prep. Proced. Int. 1998, 30, 121, and references cited therein.
14. For similar asymmetric synthesis with titanocene catalysts, see: (a) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688; (b) Idem, ibid. 1999, 121, 7026; (c) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547.
15. For similar asymmetric synthesis with titanocene catalysts, see: (a) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688; (b) Idem, ibid. 1999, 121, 7026; (c) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547.
16. For similar asymmetric synthesis with titanocene catalysts, see: (a) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688; (b) Idem, ibid. 1999, 121, 7026; (c) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547.
17. Bladon, P.; Pauson, P. L.; Brunner, H.; Eder, R. J. Organomet. Chem. 1988, 355, 449.
18. 8 (22.8 mg, 0.067 mmol) and (S)-BINAP (41.5 mg, 0.067 mmol) was flushed with carbon monoxide, and maintained under a positive pressure of carbon monoxide. DCE (4 ml) was added to the above flask at room temperature, and the reaction mixture was stirred at reflux for 2 h. A solution of a substrate 1a (70 mg, 0.333 mmol) in DCE (4 ml) was added to the above solution at reflux, and the mixture was stirred at reflux for 17 h. After cooling at room temperature, the reaction mixture was filtered through a plug of silica gel with the aid of ethyl acetate, and the filtrate was concentrated in vacuo, and the crude product was purified by preparative TLC (ethyl acetate:hexane=2:3) to give 2a (50 mg, 62% yield, 91% e.e.). The e.e. was determined by chiral HPLC (CHIRALPAK AD: 2-propanol:hexane=1:10).
19. Hua, H. J. Am. Chem. Soc. 1986, 108, 3835.
20. Brooks, D. W.; Woods, K. W. J. Org. Chem. 1987, 52, 2036.