Rhodium-catalyzed asymmetric 1,4-addition to 1-alkenylphosphonates [13]

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11591-11592

  Hayashi, Tamio ^a   Senda, Taichi ^a   Takaya, Yoshiaki ^a   Ogasawara, Masamichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE; RHODIUM;

CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033572920     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993184u     Document Type: Letter

References (24)

1. For a review on the use of phusphonates for alkene synthesis, see: Kelly, S. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1. Chapter 3.1.
2. For examples of asymmetric synthesis of biologically active phosphonates, see: (a) Blazis, V. J.; Koeller, K. J.; Spilling. C. D. J. Org. Chem. 1995, 60, 931. (b) Arai, T.; Bougauchi, M.; Sasai, H.; Shihasaki, M. J. Org. Chem. 1996, 61, 2926 and references therein. (c) Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428.
3. For examples of asymmetric synthesis of biologically active phosphonates, see: (a) Blazis, V. J.; Koeller, K. J.; Spilling. C. D. J. Org. Chem. 1995, 60, 931. (b) Arai, T.; Bougauchi, M.; Sasai, H.; Shihasaki, M. J. Org. Chem. 1996, 61, 2926 and references therein. (c) Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428.
4. For examples of asymmetric synthesis of biologically active phosphonates, see: (a) Blazis, V. J.; Koeller, K. J.; Spilling. C. D. J. Org. Chem. 1995, 60, 931. (b) Arai, T.; Bougauchi, M.; Sasai, H.; Shihasaki, M. J. Org. Chem. 1996, 61, 2926 and references therein. (c) Nagaoka, Y.; Tomioka, K. J. Org. Chem. 1998, 63, 6428.
5. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994; pp 207-212. (d) Nógrádi, M. Sterioselective Synthesis: VCH Publishers: New York, 1995; pp 213-224. (e) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995.
6. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994; pp 207-212. (d) Nógrádi, M. Sterioselective Synthesis: VCH Publishers: New York, 1995; pp 213-224. (e) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995.
7. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994; pp 207-212. (d) Nógrádi, M. Sterioselective Synthesis: VCH Publishers: New York, 1995; pp 213-224. (e) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995.
8. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994; pp 207-212. (d) Nógrádi, M. Sterioselective Synthesis: VCH Publishers: New York, 1995; pp 213-224. (e) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995.
9. For reviews, see: (a) Schmalz, H.-G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994; pp 207-212. (d) Nógrádi, M. Sterioselective Synthesis: VCH Publishers: New York, 1995; pp 213-224. (e) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley and Sons: New York, 1995.
10. For a review on 1,4-addition reactions, see: Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis: Pergamon Press: Oxford, 1992.
11. For an example of nonasymmetric addition of alkyl- and vinylcopper reagents to α,β-unsaturated phosphonates. see: Nicotra, F.; Panza, L.; Russo, G. J. Chem. Soc., Chem. Commun. 1984, 5.
12. (a) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
13. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
14. For a review on vinylphosphonates in organic synthesis, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
15. Hirao, T.; Masunaga, T.; Yaniada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
16. Arylboroxines are readily obtained by dehydration of arylboronic acids by azeotropic removal of water from their xylene solution or heating at 300 °C in vacuo. For a pertinent review, see: Lappert, M. F. Chem. Rev. 1956, 56, 959.
17. Hayashi, T.; Konishi, M.; Fukushima, M.; Mise, T.; Kagotani, M.; Tajika, M.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 180.
18. 2) did not take place (<2% yield).
19. D -103 (c 1.08, chloroform).
20. For the highly skewed structure of transition metal complexes coordinated with a binap ligand, see: Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T. Organometallics 1993, 12, 4188 and references therein.
21. Corey, E. J.; Kwiatkowski, G. T. J. Am. Chem. Soc. 1966, 88, 5654.
22. Ando, K. Tetrahedron Lett. 1995, 36, 4105.
23. The enantiomeric purities of (E)-4a and -4b were determined by GLC analysis with CP-Chirasil-dex CB (25 m).
24. D -73 (c 0.52, chloroform). The absolute configuration was assigned by the correlation with the starting (-)-(S)-3cm.