Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones

Journal of the American Chemical Society

Volumn 120, Issue 22, 1998, Pages 5579-5580

  Takaya, Yoshiaki ^a   Ogasawara, Masamichi ^a   Hayashi, Tamio ^a   Sakai, Masaaki ^b   Miyaura, Norio ^b  

^a KYOTO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; RHODIUM;

CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; JAPAN; LETTER; SYNTHESIS;

EID: 0032503611     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980666h     Document Type: Article

References (28)

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6. For recent examples for asymmetric addition of organozinc or magnesium reagents in the presence of nickel or copper catalysts, see: (a) Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620.
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16. Asymmetric addition of aryllithiums catalyzed by a chiral ligand has been reported: Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681.
17. For recent examples for catalytic asymmetric Michael addition of malonate esters, see: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
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20. For a review, see: Ojima, I. Catalytic Asymmetric Synthesis; VCH Publishers: New York, 1993.
21. Asymmetric Michael addition forming a chiral carbon center on the nucleophile has been reported to be catalyzed by a chiral bis(phosphine)-rhodium complex: (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295.
22. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.
23. The following chiral ligands were examined: 2,2'-bis(diphenylphosphino)-1,1′-binaphthyl (binap), 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis-(diphenylphosphino)butane (diop), 2,3-bis(diphenylphosphino)butane (chiraphos), 2,2 -bis[4-(isopropyl)oxazolyl]-1,1′-binaphthyl (boxax), 2-[2-(diphenylphosphino)phenyl]-4-(isopropyl)oxazoline (phox), 2-diphenylphosphino-2′-methoxy-1,1′-binaphthyl (mop).
24. D +20.5 (c 0.58, chloroform): Schultz, A. G.; Harrington, R. E. J. Am. Chem. Soc. 1991, 113, 4926.
25. 2: C, 71.36; H, 4.77. Found: C, 71.07; H, 4.76. It has been reported that the addition of a bisphosphine to Rh(acac)(cod) forms Rh(acac)(bisphosphine): Fennis, P. J.; Budzelaar, P. H. M.; Frijns, J. H. G.; Orpen, A. G. J. Organomet. Chem. 1990, 393, 287.
26. For some other substrates, the higher enantioselectvity was observed at the higher reaction temperature.
27. D -67.7 (c 1.0, chloroform): Barnhart, R. W.; Wang, X.; Noheda, P.; Bergens, S. H.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1994, 116, 1821.
28. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T. Organometallics 1993, 12, 4188 and references therein.