The first enantioselective organocatalytic Mukaiyama-Michael reaction: A direct method for the synthesis of enantioenriched γ-butenolide architecture

Journal of the American Chemical Society

Volumn 125, Issue 5, 2003, Pages 1192-1194

  Brown, Sean P ^a   Goodwin, Nicole C ^a   MacMillan, David W C ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BUTENOLIDE; LEWIS ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MUKAIYAMA MICHAEL REACTION; SYNTHESIS;

4-BUTYROLACTONE; ALDEHYDES; CATALYSIS; FURANS; IMIDAZOLES; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 0037419866     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029095q     Document Type: Article

References (83)

1. This number is based on a survey of the Beilstein database.
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22. For excellent reviews that incorporate this topic, see: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. III, Chapter 29.1. (c) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8. (d) Carreira, E. M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8B2.
23. For excellent reviews that incorporate this topic, see: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. III, Chapter 29.1. (c) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8. (d) Carreira, E. M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8B2.
24. For excellent reviews that incorporate this topic, see: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. III, Chapter 29.1. (c) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8. (d) Carreira, E. M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000; Chapter 8B2.
25. To our knowledge there have only been two reports of enantioselective catalytic Mukaiyama - Michael reactions with silyloxy furans. In both cases, electrophiles were employed that could not participate in 1,2-addition: (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (b) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570. (c) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203-10212.
26. To our knowledge there have only been two reports of enantioselective catalytic Mukaiyama - Michael reactions with silyloxy furans. In both cases, electrophiles were employed that could not participate in 1,2-addition: (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (b) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570. (c) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203-10212.
27. To our knowledge there have only been two reports of enantioselective catalytic Mukaiyama - Michael reactions with silyloxy furans. In both cases, electrophiles were employed that could not participate in 1,2-addition: (a) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (b) Kitajima, H.; Katsuki, T. Synlett 1997, 568-570. (c) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203-10212.
28. The Beilstein database reports >200 natural isolates that incorporate the 5-(1-alkyl)-5-H-furanone or 5-(1-alkyl)-5-alkyl-furanone structural motif.
29. Look, S. A.; Burch, M. T.; Fenical, W.; Zheng, Q. T.; Clardy, J. J. Org. Chem. 1985, 50, 5741-5746.
30. Rodriguez, A. D.; Shi, J. G.; Huang, S. P. D. J. Org. Chem. 1998, 63, 4425-4432.
31. Metal-mediated silyloxy furan additions to α,β-unsaturated aldehydes are typically highly selective for carbonyl addition, see: (a) von der Ohe, F.; Bruckner, R. Tetrahedron Lett. 1998, 39, 1909-1910. (b) von der Ohe, F.; Bruckner, R. New J. Chem. 2000, 24, 659-669.
32. Metal-mediated silyloxy furan additions to α,β-unsaturated aldehydes are typically highly selective for carbonyl addition, see: (a) von der Ohe, F.; Bruckner, R. Tetrahedron Lett. 1998, 39, 1909-1910. (b) von der Ohe, F.; Bruckner, R. New J. Chem. 2000, 24, 659-669.
33. To our knowledge there has been only one example of a metal-mediated 1,4-addition of enolsilanes to ambident electrophiles: Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131-4132.
34. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
35. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
36. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
37. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
38. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
39. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
40. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
41. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
42. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
43. For examples of enantioselective catalytic Mukaiyama - Michael reactions with electrophiles that cannot readily participate in 1,2-addition, see: (a) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994-1995. (b) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865-868. (c) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (d) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134-9142. (e) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480. (f) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97-100. (g) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924. (h) Bernardi, A.; Karamfilova, K.; Sanguinetti, S. Scolastico, C. Tetrahedron 1997, 53, 13009-13026. (i) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015-17028. (j) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165-1170.
44. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
45. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
46. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
47. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
48. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
49. Diels-Alder: (a) Ahrendt, K. A.; Borths, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 4243. (b) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 2458. Nitrone cycloaddition: (c) Jen, W. S.; Wiener, J. J. M.; MacMillan, D. W. C. J. Am. Chem. Soc. 2000, 122, 9874. Pyrrole substitution: (d) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 123, 4370. Indole substitution: (e) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172. Aniline substitution: (f) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
50. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
51. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
52. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
53. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
54. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
55. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
56. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
57. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
58. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
59. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
60. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
61. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
62. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
63. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
64. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
65. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
66. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
67. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
68. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
69. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an
70. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
71. For notable examples of enantioslective organocatalytic reactions, see: Aldol reaction: (a) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Agami, C.; Meyneir, F.; Puchot, C. Tetrahedron 1984, 40, 1031. (d) List, B.; Lerner, R. A.; Barbas, C. F. J. Am. Chem. Soc. 2000, 122, 2395. (e) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573. (f) List, B. J. Am. Chem. Soc. 2000, 122, 9336. Phase-transfer catalysis: (g) O'Donnell, M. J.; Bennett, W. D.; Wu, S. D. J. Am. Chem. Soc. 1989, 111, 2353. (h) Corey, E. J.; Bo, Y. X.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000. (i) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414. Epoxidation: (j) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (k) Yang, D.; Wong, M. K.; Yip, Y. C.; Wang, X. C.; Tang, M. W.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1998. 120, 5943. (l) Tu, Y.; Wang, Z. X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (m) Tian, H. Q.; She, X. G.; Shu, L. H.; Yu, H. W.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551. (n) Denmark, S. E.; Wu, Z. C. Baylis-Hillman Reaction (o) Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219. (p) Corey, E. J.; Zhang, F. Y. Org. Lett. 1999, 1, 1287. Asymmetric Strecker synthesis: (q) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867. (r) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279. (s) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157. Acyl transfer: (t) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638. Intramolecular Stetter: (u) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299. For an excellent review on enantioselective organocatalysis, see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
72. A Monte Carlo simulation using the MM3 force-field; Macromodel V6.5.
73. Asaoka, M.; Miyake, K.; Takei, H. Chem. Lett. 1977, 167.
74. To a 2-dram vial equipped with a magnetic stir bar and charged with (2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidin-4-one was added solvent, 2,4-dinitrobenzoic acid and aldehyde, and then it was placed in a bath at appropriate temperature. The solution was stirred for 10 min before the addition of siloxy furan substrate in one portion. The resulting solution was stirred at a constant temperature until the reaction was determined to be complete by a GLC conversion assay using dibenzyl ether as an internal standard. The reaction mixture was then transferred cold through a silica gel plug with ethyl acetate into a flask and carefully concentrated in vacuo. The resulting residue was purified by silica gel chromatography (solvents noted) and fractions carefully concentrated in vacuo to provide the title compounds. The enantioselectivity was determined by chiral GLC analysis.
75. Inoue, K. Fureguransu Janaru 1983, 11, 53-55.
76. Total syntheses of spiculisporic acid: Brandaenge, S.; Dahlman, O.; Lindqvist, B.; Maahlen, A.; Moerch, L. Acta Chem. Scand., Ser. B 1984, 10, 837-844.
77. (a) Birkinshaw, J. H.; Raistrick, H. Biochem. J. 1934, 228, 828-836.
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81. 2·DMF, THF.
82. 2, EtOAc.
83. (c) 4 N NaOH, 100 °C then adjusted to pH = 1 with 1 N HCl, 100 °C.