Catalytic enantioselective synthesis of (20s)-camptothecin intermediates using cyanosilylation of ketones promoted by D-glucose-derived lanthanide catalyst

Heterocycles

Volumn 59, Issue 1, 2003, Pages 369-385

  Yabu, Kazuo ^a   Masumoto, Shuji ^a   Kanai, Motomu ^a,b   Du, Wu ^b   Curran, Dennis P ^b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPTOTHECIN DERIVATIVE; CYANOHYDRIN; GADOLINIUM; GLUCOSE; KETONE DERIVATIVE; LANTHANIDE; LIGAND; SAMARIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CYANOSILYLATION; ENANTIOSELECTIVITY; REACTION ANALYSIS; SILYLATION; SYNTHESIS;

EID: 0037224343     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-s49     Document Type: Article

References (18)

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7. For our (R)-selective catalytic enantioselective cyanosilylation of ketones, see: a) Y. Hamashima, M. Kanai, and M. Shibasaki, J. Am. Chem. Soc., 2000, 122, 7412. b) Y. Hamashima, M. Kanai, and M. Shibasaki, Tetrahedron Lett., 2001, 42, 691. For our (S)-selective catalytic enantioselective cyanosilylation of ketones, see: c) K. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D. P. Curran, and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 9908.
8. For our (R)-selective catalytic enantioselective cyanosilylation of ketones, see: a) Y. Hamashima, M. Kanai, and M. Shibasaki, J. Am. Chem. Soc., 2000, 122, 7412. b) Y. Hamashima, M. Kanai, and M. Shibasaki, Tetrahedron Lett., 2001, 42, 691. For our (S)-selective catalytic enantioselective cyanosilylation of ketones, see: c) K. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D. P. Curran, and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 9908.
9. For our (R)-selective catalytic enantioselective cyanosilylation of ketones, see: a) Y. Hamashima, M. Kanai, and M. Shibasaki, J. Am. Chem. Soc., 2000, 122, 7412. b) Y. Hamashima, M. Kanai, and M. Shibasaki, Tetrahedron Lett., 2001, 42, 691. For our (S)-selective catalytic enantioselective cyanosilylation of ketones, see: c) K. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D. P. Curran, and M. Shibasaki, J. Am. Chem. Soc., 2001, 123, 9908.
10. For other examples of catalytic enantioselective cyanosilylation of ketones, see a) H. Deng, M. P. Isler, M. L. Snapper, and A. H. Hoveyda, Angew. Chem., Int. Ed., 2002, 41, 1009. b) S.-K. Tian and L. Deng, J. Am. Chem. Soc., 2001, 123, 6195. c) Y. N. Belokon', B. Green, N. S. Ikonnikov, M. North, T. Parsons, and V. I. Tararov, Tetrahedron, 2001, 57, 771.
11. For other examples of catalytic enantioselective cyanosilylation of ketones, see a) H. Deng, M. P. Isler, M. L. Snapper, and A. H. Hoveyda, Angew. Chem., Int. Ed., 2002, 41, 1009. b) S.-K. Tian and L. Deng, J. Am. Chem. Soc., 2001, 123, 6195. c) Y. N. Belokon', B. Green, N. S. Ikonnikov, M. North, T. Parsons, and V. I. Tararov, Tetrahedron, 2001, 57, 771.
12. For other examples of catalytic enantioselective cyanosilylation of ketones, see a) H. Deng, M. P. Isler, M. L. Snapper, and A. H. Hoveyda, Angew. Chem., Int. Ed., 2002, 41, 1009. b) S.-K. Tian and L. Deng, J. Am. Chem. Soc., 2001, 123, 6195. c) Y. N. Belokon', B. Green, N. S. Ikonnikov, M. North, T. Parsons, and V. I. Tararov, Tetrahedron, 2001, 57, 771.
13. For the preliminary communication, see ref. 5(c) and: K. Yabu, S. Masumoto, M. Kanai, D. P. Curran, and M. Shibasaki, Tetrahedron Lett., 2002, 43, 2923.
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15. It is noteworthy that the optimum lanthanide metal is gadolinium in the catalytic enantioselective cyanosilylation of simple ketones such as acetophenone.
16. S. Masumoto, K. Yabu, M. Kanai, and M. Shibasaki, Tetahedron Lett., 2002, 43, 2919.
17. For example, the Sm-catalyst (5 mol %) derived from ligand (14) gave 12 in 96% yield with 81% ee (-40 °C, 20 h).
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