Palladium-catalyzed asymmetric allylic alkylation of α-aryl ketones

Angewandte Chemie - International Edition

Volumn 41, Issue 18, 2002, Pages 3492-3495

  Trost, Barry M ^a   Schroeder, Gretchen M ^a   Kristensen, Jesper ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Aryl ketones; Asymmetric catalysis; Enantioselectivity; Ligand effects; Palladium

Indexed keywords

ALKYLATION; CATALYSIS; CONFORMATIONS; PALLADIUM; SYNTHESIS (CHEMICAL);

QUATERNARY CENTERS;

KETONES;

1,8 DIAZABICYCLO[5.4.0]UNDEC 7 ENE; 2 TETRALONE; ALKYL ARYL KETONE; BETA-TETRALONE; BICYCLO COMPOUND; KETONE; LIGAND; METAL ION; NAPHTHALENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATIONAL TRANSITION; ENANTIOSELECTIVITY; REACTION ANALYSIS;

ALKYLATION; CATALYSIS; KETONES; NAPHTHALENES; PALLADIUM; TETRALONES;

EID: 0037119732     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20020916)41:18<3492::AID-ANIE3492>3.0.CO;2-P     Document Type: Article

References (43)

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29. The compatibility of ketone enolates with palladium has also been demonstrated in the palladium-catalyzed arylation of ketone enolates. This method also provides an alternative catalytic asymmetric route to quaternary centers bearing an aryl group. see T. Hamada, A. Chieffi, J. Arhman, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1261; J. M. Fox, X. Huang, A. Chieffi, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 1360; M. Kawatsura, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 1473; J. Ahman, J. P. Wolfe, M. V. Troutman, M. Palucki, S. L. Buchwald, J. Am. Chem. Soc 1998, 120, 1918; M. Palucki, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 11108.
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36. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.
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38. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.
39. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.
40. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.
41. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.
42. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.
43. C. Chassaing, A. Haudrechy, Y. Langlois, Tetrahedron Lett. 2000, 41, 785; A. Haudrechy, C. Chassaing, C. Riche, Y. Langlois, Tetrahedron 2000, 56, 3181; S. Kaneko, T. Yoshino, T. Katoh, S. Terashima, Tetrahedron 1998, 54, 5471; X.-C. He, B. Wang, D. Bai, Tetrahedron Lett. 1998, 39, 411; A. P. Kozikowski, Y. Xia, E. R. Reddy, W. Tuckmantel, I. Hanin, X. C. Tang, J. Org. Chem. 1991, 56, 4636; T. Hayashi, K. Kaneshira, T Hagihara, M. Kumada, J. Org. Chem. 1988, 53, 113; see also D. L. Bai, X. C. Tang, X. C. He, Curr. Med. Chem. 2000, 7, 355. For analogues, see P. Camps, E. Gómez, D. Muñoz-Torrero, M. Arnó, Tetrahedron: Asymmetry 2001, 12, 2909.