Rhodium-catalyzed asymmetric 1,4-addition of arylboron compounds generated in situ from aryl bromides

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 6957-6961

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; KETONE; LITHIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM COMPLEX; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033578885     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01412-4     Document Type: Article

References (12)

1. Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229.
2. Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
3. Takaya, Y.; Ogasawara, M.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8479.
4. (a) Brown, H. C.; Gupta, S. K. J. Am. Chem. Soc. 1975, 97, 5249.
5. (b) Brown, H. C.; Bhat, N. G.; Somayaji, V. Organometallics 1983, 2, 1311.
6. (c) Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316.
7. (d) Hawthorne, M. F. J. Am. Chem. Soc. 1958, 80, 4291.
8. The absolute configuration of the arylation product obtained with (S)-binap ligand is expected to be (S) according to an empirical rule shown in Ref. 2.
9. 14O: C, 85.68; H, 6.71. Found: C, 85.75; H, 6.83. For 3an, 3ao, 3ap, 3bn, 3cn, and 3dn, see Ref. 2.
10. 2 (3.1 mg, 12 μmol) and (S)-binap (9.0 mg, 14 μmol) in dioxane (2 mL). The whole mixture was heated at 100°C for 5 h. Addition of saturated aqueous sodium hydrogen carbonate followed by ethyl acetate extraction and silica gel chromatography (hexane/ethyl acetate=5/1) gave 70 mg (>99% yield) of (S)-3-phenylcyclohexanone (3an), whose enantiomeric purity was determined to be 99% ee by HPLC analysis with a chiral stationary phase column.
11. For a review on organoboronic acids and esters: Lappert, M. F. Chem. Rev. 1956, 56, 959.
12. Torssell, K. Acta Chem. Scand. 1954, 8, 1779.