Asymmetric coupling of phenols with arylleads [2]

Journal of the American Chemical Society

Volumn 121, Issue 38, 1999, Pages 8943-8944

  Saito, Susumu ^a   Kano, Taichi ^a   Muto, Hiroo ^a   Nakadai, Masakazu ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; BRUCINE; CYCLOHEXYLAMINE DERIVATIVE; ETHYLENEDIAMINE; LEAD; PHENOL DERIVATIVE; QUINUCLIDINE; STRYCHNINE; TERPHENYL DERIVATIVE; TOLUENE;

CATALYST; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; LETTER; OPTICAL ROTATION; STEREOCHEMISTRY;

EID: 0033615324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990646v     Document Type: Letter

References (23)

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7. See ref 7 in Supporting Information.
8. (a) Tamao, K.; Sumitani, K.; Kiso, Y.; Zembayashi, N.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
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10. See ref 8 in Supporting Information.
11. See ref 9 in Supporting Information.
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13. (b) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 58, 1147.
14. For the preparation of aryllead compounds 2a-d, see: (c) Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans, 1 1990, 715.
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18. Barton, D. H. R.; Donnelly, D. M. X.; Guiry, P. J.; Finet, J.-P. J. Chem. Soc., Perkin Trans. 1 1994, 2921.
19. (a) Saito, S.; Hatanaka, K.; Kano, T.; Yamamoto, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 3378.
20. For preliminary preparation of 3a,b, see: (b) Saito, S.; Kano, T.; Hatanaka, K.; Yamamoto, H. J. Org. Chem. 1997, 62, 5651.
21. 2,6-Dibromo-3,5-dimethylanisole (17) and boronic acids 18a-c were subjected to Suzuki coupling to give the corresponding terphenyl adducts 19a-c with moderate yields and diastereoselectivities. See Supporting Information and also ref 10b.
22. 1H NMR and HPLC analysis. See ref 10b.
23. The ee % of each adduct was determined by chiral HPLC analysis. The rather low yield by slow reaction with strychnine is probably due to its insolubility in toluene.