Highly Enantioselective Synthesis of 1,2-Amino Alcohol Derivatives via Proline-Catalyzed Mannich Reaction

Synlett

Volumn , Issue 12, 2003, Pages 1903-1905

  Pojarliev, Peter ^a   Biller, William T ^a   Martin, Harry J ^a   List, Benjamin ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Aminoalcohols; Multicomponent reactions; Organocatalysis; Oxazolidinones

Indexed keywords

AMINOALCOHOL; OXAZOLIDINONE DERIVATIVE; PROLINE;

ARTICLE; ASYMMETRIC CATALYSIS; BAEYER VILLIGER REACTION; CHEMICAL ANALYSIS; ENANTIOSELECTIVITY; MANNICH REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0142059750     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41491     Document Type: Article

References (31)

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14. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
15. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
16. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
17. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
18. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
19. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
20. For selected other methods for the synthesis of 2-substituted 2-amino ethanols such as 3, see: (a) Smith, G. A.; Gawley, R. E. Org. Synth. 1985, 63, 136. (b) Meyers, A. I.; McKennon, M. J. J. Org. Chem. 1993, 58, 3568. (c) Morita, T.; Nagasawa, Y.; Yahiro, S.; Matsunaga, H.; Kunieda, T. Org. Lett. 2001, 3, 897. (d) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275. (e) Takacs, J. M.; Jaber, M. R.; Vellekoop, A. S. J. Org. Chem. 1998, 63, 2742. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Enders, D.; Reinhold, U. Liebigs Ann. 1996, 11. (h) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051. (i) Youn, S. W.; Choi, J. Y.; Kim, Y. H. Chirality 2000, 12, 404.
21. For elegant examples of such α-hydroxy ketone cleavages, see: (a) Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. (b) Kirihara, M.; Takizawa, S.; Momose, T. J. Chem. Soc., Perkin Trans. 1 1998, 7. (c) Palomo, C.; Oiarbide, M.; Gonzalez-Rego, M. C.; Sharma, A. K.; Garcia, J. M.; Gonzalez, A.; Landa, C.; Linden, A. Angew. Chem., Int. Ed. 2000, 39, 1063.
22. For elegant examples of such α-hydroxy ketone cleavages, see: (a) Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. (b) Kirihara, M.; Takizawa, S.; Momose, T. J. Chem. Soc., Perkin Trans. 1 1998, 7. (c) Palomo, C.; Oiarbide, M.; Gonzalez-Rego, M. C.; Sharma, A. K.; Garcia, J. M.; Gonzalez, A.; Landa, C.; Linden, A. Angew. Chem., Int. Ed. 2000, 39, 1063.
23. For elegant examples of such α-hydroxy ketone cleavages, see: (a) Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499. (b) Kirihara, M.; Takizawa, S.; Momose, T. J. Chem. Soc., Perkin Trans. 1 1998, 7. (c) Palomo, C.; Oiarbide, M.; Gonzalez-Rego, M. C.; Sharma, A. K.; Garcia, J. M.; Gonzalez, A.; Landa, C.; Linden, A. Angew. Chem., Int. Ed. 2000, 39, 1063.
24. (a) Ziegler, F. E.; Metcalf, C. A. III; Nangia, A.; Schulte, G. J. Am. Chem. Soc. 1993, 115, 2581.
25. (b) MCPBA was less efficient in these reactions.
26. See for example: (a) Ziegler, F. E.; Kim, H. Tetrahedron Lett. 1993, 34, 7669. (b) Matsutani, H.; Ichikawa, S.; Yaruva, J.; Kusumoto, T.; Hiyama, T. J. Am. Chem. Soc. 1997, 119, 4541. (c) Kim, C.; Hoang, R.; Theodorakis, E. A. Org. Lett. 1999, 1, 1295.
27. See for example: (a) Ziegler, F. E.; Kim, H. Tetrahedron Lett. 1993, 34, 7669. (b) Matsutani, H.; Ichikawa, S.; Yaruva, J.; Kusumoto, T.; Hiyama, T. J. Am. Chem. Soc. 1997, 119, 4541. (c) Kim, C.; Hoang, R.; Theodorakis, E. A. Org. Lett. 1999, 1, 1295.
28. See for example: (a) Ziegler, F. E.; Kim, H. Tetrahedron Lett. 1993, 34, 7669. (b) Matsutani, H.; Ichikawa, S.; Yaruva, J.; Kusumoto, T.; Hiyama, T. J. Am. Chem. Soc. 1997, 119, 4541. (c) Kim, C.; Hoang, R.; Theodorakis, E. A. Org. Lett. 1999, 1, 1295.
29. 1
30. (a) List, B. J. Am. Chem. Soc. 2002, 5656.
31. (b) Also see: Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2002, 41, 1790.