Asymmetric Allylic Amination in Water Catalyzed by an Amphiphilic Resin-Supported Chiral Palladium Complex

Organic Letters

Volumn 6, Issue 2, 2004, Pages 281-283

  Uozumi, Yasuhiro ^a   Tanaka, Hirotaka ^a   Shibatomi, Kazutaka ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; AMPHOPHILE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; COPOLYMER; DIBENZYLAMINE; INDOLE DERIVATIVE; MACROGOL; METHYL 5 METHOXYCARBONYLCYCLOHEXEN 2 YLCARBONATE; METHYLCYCLOHEPTEN 2 YLCARBONATE; METHYLCYCLOHEXEN 2 YLCARBONATE; METHYLCYCLOHEXENYLCARBONATE; PALLADIUM COMPLEX; POLYSTYRENE; RESIN; TERT BUTYL 5 METHOXYCARBONYLOXY 1,2,5,6 TETRAHYDROPYRIDINEDICARBOXYLATE; UNCLASSIFIED DRUG; WATER;

AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; METHODOLOGY;

EID: 0842328408     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036264i     Document Type: Article

References (37)

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3. For reviews, see: (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; Wiley-VCH: New York, 1997. (b) Grieco, P. A. Organic Synthesis in Water; Kluwer Academic Publishers: Dordrecht, 1997. (c) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
4. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
5. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
6. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
7. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
8. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
9. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
10. For reviews, see: (a) Bailey, D. C.; Langer, S. H. Chem. Rev. 1981, 81, 109. (b) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217. (c) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035. (d) Dörwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000. (e) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S. ; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815. (f) Leadbeater, N. E.; Marco, M. Chem. Rev. 2002, 102, 3217. (h) McNamara, C. A.; Dixon, M. J.; Bradley, M. Chem. Rev. 2002, 102, 3275.
11. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
12. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
13. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
14. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
15. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
16. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
17. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
18. For studies on polymer-supported palladium catalysts reported by the author's group, see: (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1997, 38, 3557 (π-allylic substitution). (b) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55, 14341 (π-allylic substitution). (c) Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384 (cross-coupling). (d) Uozumi, Y.; Watanabe, T. J. Org. Chem. 1999, 64, 6921 (carbonylation reaction). (e) Uozumi, Y.; Nakai, Y. Org. Lett. 2002, 4, 2997 (Suzuki coupling). (f) Uozumi, Y.; Kimura, T. Synlett 2002, 2045 (Heck reaction). (g) Hocke, H.; Uozumi, Y. Synlett 2002, 2049 (Wacker reaction). (h) Uozumi, Y.; Kobayashi, Y. Heterocycles 2003, 59, 71 (Sonogashira reaction).
19. For a recent review on asymmetric π-allylic substitution, see: (a) Acemoglu, L.; Williams, J. M. J. Handbook of Organopalladium Chemistry, p 1945;Negishi, E., Ed.; Wiley, New York, 2002. (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
20. For a recent review on asymmetric π-allylic substitution, see: (a) Acemoglu, L.; Williams, J. M. J. Handbook of Organopalladium Chemistry, p 1945;Negishi, E., Ed.; Wiley, New York, 2002. (b) Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921.
21. For recent reviews on heterogeneous asymmetric catalysis, see: (a) Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, 2000. (b) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
22. For recent reviews on heterogeneous asymmetric catalysis, see: (a) Chiral Catalyst Immobilization and Recycling; De Vos, D. E., Vankelecom, I. F. J., Jacobs, P. A., Eds.; Wiley-VCH: Weinheim, 2000. (b) Fan, Q.-H.; Li, Y.-M.; Chan, A. S. C. Chem. Rev. 2002, 102, 3385.
23. For a review on asymmetric catalysis in water, see: Lindström, U. M. Chem. Rev. 2002, 102, 2751.
24. (a) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303.
25. (b) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919.
26. (c) Shibatomi, K.; Uozumi, Y. Tetrahedron: Asymmetry 2002, 13, 1769.
27. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
28. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
29. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
30. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
31. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
32. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
33. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
34. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
35. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
36. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.
37. For asymmetric π-allylic substitution of cycloalkenyl esters with high stereoselectivity, see: (a) Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1994, 116, 4089. (b) Knühl, G.; Sennhenn, P.; Helmchen, G. J. Chem. Soc., Chem. Commun. 1995, 1845. (c) Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047. (d) Gilbertson, S.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750. (e) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Org. Chem. 1999, 64, 2994. (f) Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gangne, M. R. J. Am. Chem. Soc. 2000, 122, 7905. (g) Saitoh, A.; Achiwa, K.; Tanaka, K.; Morimoto, T. J. Org. Chem. 2000, 65, 4227. (h) Hou, D.-R.; Reibenspies, J. H.; Burgess, K. J. Org. Chem. 2001, 66, 206. (i) Hamada, Y.; Sakaguchi, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297. (j) Xiao, L.; Weissensteiner, W.; Mereiter, K.; Widhalm, M. J. Org. Chem. 2002, 67, 2206. (k) Agarkov, A.; Uffman, E. W.; Gilbertson, S. R. Org. Lett. 2003, 5, 2091.