Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones

Journal of the American Chemical Society

Volumn 130, Issue 5, 2008, Pages 1576-1577

  Nishimura, Takahiro ^a   Guo, Xun Xiang ^a   Uchiyama, Nanase ^a   Katoh, Taisuke ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; KETONE DERIVATIVE; LIGAND; PHOSPHINE; RHODIUM; SILYLACETYLENE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; SONOGASHIRA REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 38949195266     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710540s     Document Type: Article

References (26)

1. (a) Yoshida, K.; Hayashi, T. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 3.
2. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
3. (c) Hayashi, T. Bull. Chem. Soc. Jpn. 2004, 77, 13.
4. (d) Hayashi, T. Pure Appl. Chem. 2004, 76, 465.
5. (e) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313.
6. (f) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
7. (a) Fujimori, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 4964.
8. (b) Knöpfel, T. F.; Zarotti, P.; Ichikawa, T.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 9682.
9. (c) Kwak, Y.-S.; Corey, E. J. Org. Lett. 2004, 6, 3385.
10. (d) Wu, T. R.; Chong, J. M. J. Am. Chem. Soc. 2005, 127, 3244.
11. For recent examples of rhodium-catalyzed dimerization of alkynes, see: (a) Nishimura, T.; Guo, X.-X.; Ohnishi, K.; Hayashi, T. Adv. Synth. Catal. 2007, 349, 2669.
12. (b) Katagiri, T.; Tsurugi, H.; Funayama, A.; Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 830.
13. (c) Weng, W.; Guo, C.; Çelenligil-Çetin, R.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2006, 197.
14. (d) Lee, C.-C.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. Organometallics 2005, 24, 136 and references therein.
15. Catalytic conjugate addition of terminal acetylenes has been reported only for β-unsubstituted enones. (a) Nikishin, G. I.; Kovalev, I. P. Tetrahedron Lett. 1990, 31, 7063.
16. (b) Lerum, R. V.; Chisholm, J. D. Tetrahedron Lett. 2004, 45, 6591.
17. Nishimura, T.; Katoh, T.; Takatsu, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 14158.
18. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264. DTBM-segphos; 5,5′-bis{di(3,5-di-tert-butyl-4-methoxyphenyl) phosphino}-4,4′-bi-1,3-benzodioxole. Segphos; 5,5′- bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole.
19. 2 is more convenient to use because of its facile ligand exchange between the coordinated ethylene and a bisphosphine ligand.
20. Binap; 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.
21. 1H NMR of the crude reaction mixture.
22. Senda, T.; Ogasawara, M.; Hayashi, T. J. Org. Chem. 2001, 66, 6852. DMM-binap; 2,2′-bis{bis(3,5-dimethyl-4-methoxyphenyl) phosphino}-1,1′-binaphthyl.
23. 2O).
24. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
25. (a) Barral, K.; Moorhouse, A. D.; Moses, J. E. Org. Lett. 2007, 9, 1809.
26. (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.