2,2′-Bis(diarylstibano)-1,1′-binaphthyls (BINASbs); a useful chiral ligand for palladium-catalyzed asymmetric allylic alkylation, and the structure of a BINASb-PdCl2 complex

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6217-6220

  Yasuike, Shuji ^a   Okajima, Satoru ^a   Yamaguchi, Kentaro ^b   Kurita, Jyoji ^a  

^a HOKURIKU UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

2,2 bis(diarylstibano) 1,1 binaphthyl (BINASb); Antimony and compounds; Asymmetric allylic alkylations; Asymmetric reactions; X ray crystal structures

Indexed keywords

1,3 DIPHENYLPROP 2 EN 1 YLACETATE; ACETAMIDE; ACETIC ACID DERIVATIVE; DIMETHYLMALONATE; MALONIC ACID DERIVATIVE; NAPHTHYL GROUP; PALLADIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; X RAY ANALYSIS;

EID: 0042371859     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01544-2     Document Type: Article

References (68)

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2. For reviews including transition metal-catalyzed asymmetric allylic substitution, see: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (b) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871; (c) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122; (d) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
3. For reviews including transition metal-catalyzed asymmetric allylic substitution, see: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (b) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871; (c) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122; (d) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
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5. For reviews including transition metal-catalyzed asymmetric allylic substitution, see: (a) Trost, B. M.; Lee, C. In Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp. 593-649; (b) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857-871; (c) Frost, C. G.; Howarth, J.; Williams, J. M. J. Tetrahedron: Asymmetry 1992, 3, 1089-1122; (d) Trost, B. M.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395-422; (e) Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1-14.
6. For recent selected examples of palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl derivatives, see: (a) Trost, B. M.; Richard, C. B. J. Am. Chem. Soc. 1994, 116, 4089-4090; (b) Kudis, S.; Helmchen, U. Angew. Chem., Int. Ed. 1998, 37, 3047-3050; (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 2750-2752; (d) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240; (e) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206-215; (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919-2920; (g) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206-2214; (h) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1767-1772.
7. For recent selected examples of palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl derivatives, see: (a) Trost, B. M.; Richard, C. B. J. Am. Chem. Soc. 1994, 116, 4089-4090; (b) Kudis, S.; Helmchen, U. Angew. Chem., Int. Ed. 1998, 37, 3047-3050; (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 2750-2752; (d) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240; (e) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206-215; (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919-2920; (g) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206-2214; (h) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1767-1772.
8. For recent selected examples of palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl derivatives, see: (a) Trost, B. M.; Richard, C. B. J. Am. Chem. Soc. 1994, 116, 4089-4090; (b) Kudis, S.; Helmchen, U. Angew. Chem., Int. Ed. 1998, 37, 3047-3050; (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 2750-2752; (d) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240; (e) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206-215; (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919-2920; (g) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206-2214; (h) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1767-1772.
9. For recent selected examples of palladium-catalyzed asymmetric allylic alkylation of cycloalkenyl derivatives, see: (a) Trost, B. M.; Richard, C. B. J. Am. Chem. Soc. 1994, 116, 4089-4090; (b) Kudis, S.; Helmchen, U. Angew. Chem., Int. Ed. 1998, 37, 3047-3050; (c) Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. Engl. 1999, 38, 2750-2752; (d) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227-4240; (e) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206-215; (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919-2920; (g) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206-2214; (h) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1767-1772.
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