Direct catalytic asymmetric enolexo aldolizations

Angewandte Chemie - International Edition

Volumn 42, Issue 24, 2003, Pages 2785-2788

  Pidathala, Chandrakala ^a   Hoang, Linh ^a   Vignola, Nicola ^a   List, Benjamin ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Aldol reaction; Amino acids; Asymmetric catalysis; Organocatalysis

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; SUBSTITUTION REACTIONS;

ALDOLIZATIONS;

AROMATIC COMPOUNDS;

AMINO ACID; CARBONYL DERIVATIVE; CYCLOHEXANE DERIVATIVE; HEPTANE; HEPTANEDIAL; PROLINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

ALDEHYDES; CATALYSIS;

EID: 0038729533     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351266     Document Type: Article

References (67)

1. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
2. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
3. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
4. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
5. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
6. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
7. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
8. For some recent reviews and accounts, see: a) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325-335; b) T. D. Machajewski, C.-H. Wong, Angew. Chem. 2000, 112, 1406-1430; Angew. Chem. Int. Ed. 2000, 39, 1352-1374; c) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595-1601; d) S. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432-440; e) S. G. Nelson, Tetrahedron: Asymmetry 1998, 9, 357-389; f) M. Shibasaki, H. Sasai, T. Arai, T. Iida, Pure Appl. Chem. 1998, 70, 1027-1034; g) E. M. Carreira, R. A. Singer, Drug Discovery Today 1996, 1, 145-150.
9. a) Z. G. Hajos, D. R. Parrish, German Patent DE 2102623, 1971;
10. b) U. Eder, G. R. Sauer, R. Wiechert, German Patent DE 2014757, 1971;
11. c) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493; Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
12. c) U. Eder, G. Sauer, R. Wiechert, Angew. Chem. 1971, 83, 492-493; Angew. Chem. Int. Ed. Engl. 1971, 10, 496-497;
13. d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; Related enantiogroup-differentiating aldol cyclodehydrations have been described, see: C. Agami, N. Platzer, H. Sevestre, Bull. Soc. Chim. Fr. 1987, 2, 358-360.
14. d) Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621; Related enantiogroup-differentiating aldol cyclodehydrations have been described, see: C. Agami, N. Platzer, H. Sevestre, Bull. Soc. Chim. Fr. 1987, 2, 358-360.
15. Reviews: a) N. Cohen, Acc. Chem. Res. 1976, 9, 512-517;
16. b) K. Drauz, A. Kleemann, J. Martens, Angew. Chem. 1982, 94, 590-613; Angew. Chem. Int. Ed. Engl. 1982, 21, 584-608;
17. b) K. Drauz, A. Kleemann, J. Martens, Angew. Chem. 1982, 94, 590-613; Angew. Chem. Int. Ed. Engl. 1982, 21, 584-608;
18. c) E. R. Jarvo, S. J. Miller Tetrahedron 2002, 58, 2481-2495;
19. d) B. List, Tetrahedron 2002, 58, 5572-5590;
20. e) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864; Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
21. e) P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840-3864; Angew. Chem. Int. Ed. 2001, 40, 3726-3748.
22. a) J. E. Baldwin, M. J. Lusch, Tetrahedron 1982, 38, 2939-2947;
23. b) J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736.
24. Cycloaldolizations are formally enolexo- or enolendo-exo-trig processes. However, since all intramolecular aldolizations are by definition exo-trig processes, we refer to these processes simply as enolexo or enolendo aldolizations.
25. For a proline-catalyzed enolexo aldolization in a dynamic kinetic resolution, see: R. B. Woodward et al., J. Am. Chem. Soc. 1981, 103, 3210-3213; Also see: C. Agami, N. Platzer, C. Puchot, H. Sevestre, Tetrahedron 1987, 43, 1091-1098.
26. For a proline-catalyzed enolexo aldolization in a dynamic kinetic resolution, see: R. B. Woodward et al., J. Am. Chem. Soc. 1981, 103, 3210-3213; Also see: C. Agami, N. Platzer, C. Puchot, H. Sevestre, Tetrahedron 1987, 43, 1091-1098.
27. For selected non-enantioselective variants, see: a) R. B. Woodward, F. Sondheimer, D. Taub, K. Heusler, W. M. MacLamore, J. Am. Chem. Soc. 1952, 74, 4223-4251; b) E. J. Corey, R. L. Danheiser, S. Chandrasekaran, P. Siret, G. E. Keck, J. L. Gras, J. Am. Chem. Soc. 1978, 100, 8031-8034; c) H. Hagiwara, H. Ono, N. Komatsubara, T. Hoshi, T. Suzuki, M. Ando, Tetrahedron Lett. 1999, 40, 6627-6630.
28. For selected non-enantioselective variants, see: a) R. B. Woodward, F. Sondheimer, D. Taub, K. Heusler, W. M. MacLamore, J. Am. Chem. Soc. 1952, 74, 4223-4251; b) E. J. Corey, R. L. Danheiser, S. Chandrasekaran, P. Siret, G. E. Keck, J. L. Gras, J. Am. Chem. Soc. 1978, 100, 8031-8034; c) H. Hagiwara, H. Ono, N. Komatsubara, T. Hoshi, T. Suzuki, M. Ando, Tetrahedron Lett. 1999, 40, 6627-6630.
29. For selected non-enantioselective variants, see: a) R. B. Woodward, F. Sondheimer, D. Taub, K. Heusler, W. M. MacLamore, J. Am. Chem. Soc. 1952, 74, 4223-4251; b) E. J. Corey, R. L. Danheiser, S. Chandrasekaran, P. Siret, G. E. Keck, J. L. Gras, J. Am. Chem. Soc. 1978, 100, 8031-8034; c) H. Hagiwara, H. Ono, N. Komatsubara, T. Hoshi, T. Suzuki, M. Ando, Tetrahedron Lett. 1999, 40, 6627-6630.
30. For two indirect catalytic enantioselective enolexo aldolizations, see: a) Romo's organocatalytic asymmetric syn-diastereo-specific intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL): G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; b) Krische's catalytic asymmetric carbometallative aldol cycloreduction, which is a tandem catalytic asymmetric conjugate addition followed by a syn-diastereo-selective enolexo aldolization: D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111.
31. For two indirect catalytic enantioselective enolexo aldolizations, see: a) Romo's organocatalytic asymmetric syn-diastereo-specific intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL): G. S. Cortez, R. L. Tennyson, D. Romo, J. Am. Chem. Soc. 2001, 123, 7945-7946; b) Krische's catalytic asymmetric carbometallative aldol cycloreduction, which is a tandem catalytic asymmetric conjugate addition followed by a syn-diastereo-selective enolexo aldolization: D. F. Cauble, J. D. Gipson, M. J. Krische, J. Am. Chem. Soc. 2003, 125, 1110-1111.
32. a) B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396;
33. b) W. Notz, B. List, J. Am. Chem. Soc. 2000, 122, 7386-7387;
34. c) B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575.
35. a) A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 6798-6799 (This important paper describes an intermolecular variant of the reaction discussed here);
36. b) A. Córdova, W. Notz, C. F. Barbas III, J. Org. Chem. 2002, 67, 301-303;
37. c) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620-621, Also see: A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793; N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689; Angew. Chem. Int. Ed. 2003, 42, 661-665.
38. c) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620-621, Also see: A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793; N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689; Angew. Chem. Int. Ed. 2003, 42, 661-665.
39. c) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620-621, Also see: A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793; N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689; Angew. Chem. Int. Ed. 2003, 42, 661-665.
40. c) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620-621, Also see: A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793; N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689; Angew. Chem. Int. Ed. 2003, 42, 661-665.
41. c) A. Bøgevig, N. Kumaragurubaran, K. A. Jørgensen, Chem. Commun. 2002, 620-621, Also see: A. Bøgevig, K. Juhl, N. Kumaragurubaran, W. Zhuang, K. A. Jørgensen, Angew. Chem. 2002, 114, 1868-1871; Angew. Chem. Int. Ed. 2002, 41, 1790-1793; N. Halland, P. S. Aburel, K. A. Jørgensen, Angew. Chem. 2003, 115, 685-689; Angew. Chem. Int. Ed. 2003, 42, 661-665.
42. For the first proline-catalyzed asymmetric intermolecular Mannich, Michael, and α-amination reactions, see a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833; c) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425; d) B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657.
43. For the first proline-catalyzed asymmetric intermolecular Mannich, Michael, and α-amination reactions, see a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833; c) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425; d) B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657.
44. For the first proline-catalyzed asymmetric intermolecular Mannich, Michael, and α-amination reactions, see a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833; c) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425; d) B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657.
45. For the first proline-catalyzed asymmetric intermolecular Mannich, Michael, and α-amination reactions, see a) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337; b) B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827-833; c) B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425; d) B. List, J. Am. Chem. Soc. 2002, 124, 5656-5657.
46. a) For recent highlights, see: a) M. Movassaghi, E. N. Jacobsen, Science 2003, 298, 1904-1905;
47. b) S. Borman, Chem. Eng. News 2002, 80, 35-37;
48. c) H. Gröger, J. Wilken, Angew. Chem. 2001, 113, 545-548; Angew. Chem, Int. Ed. 2001, 40, 529-532.
49. c) H. Gröger, J. Wilken, Angew. Chem. 2001, 113, 545-548; Angew. Chem, Int. Ed. 2001, 40, 529-532.
50. a) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 9922-9923;
51. b) S. Bahmanyar, K. N. Houk, J. Am. Chem. Soc. 2001, 123, 11273-11283;
52. c) S. Bahmanyar, K. N. Houk, H. J. Martin, B. List, J. Am. Chem. Soc. 2003, 125, 2475-2479;
53. d) L. Hoang, S. Bahmanyar, K. N. Houk, B. List, J. Am. Chem. Soc. 2003, 125, 16-17.
54. For additional supporting density functional theory calculations, see: a) K. N. Rankin, J. W. Gauld, R. J. Boyd, J. Phys. Chem. A 2002, 106, 5155-5159; b) M. Arnó, L. R. Domingo, Theor. Chem. Acc. 2002, 108, 232-239.
55. For additional supporting density functional theory calculations, see: a) K. N. Rankin, J. W. Gauld, R. J. Boyd, J. Phys. Chem. A 2002, 106, 5155-5159; b) M. Arnó, L. R. Domingo, Theor. Chem. Acc. 2002, 108, 232-239.
56. B. List, Synlett 2001, 1675-1686.
57. M. Daumas, Y. Vo-Quang, L. Vo-Quang, F. Le Goffic, Synthesis 1989, 64-65.
58. 2, LiOH, THF).
59. The analogous proline-catalyzed 5-enolexo aldolization of hexanedial is less selective (d.r. = 2:1; ee(anti) = 79%, ee(syn) = 37%).
60. 3 (R. G. Salomon, M. F. Salomon, J. Org. Chem. 1975, 40, 1488-1492; P. Tundo, S. Memoli, M. Selva, WO 02/14257, 2000.) Diisobutylaluminium hydride reduction (or LAH reduction followed by PCC oxidation) of the resulting diesters then provided the desired pimelaldehydes 1 in acceptable overall yields.
61. 3 (R. G. Salomon, M. F. Salomon, J. Org. Chem. 1975, 40, 1488-1492; P. Tundo, S. Memoli, M. Selva, WO 02/14257, 2000.) Diisobutylaluminium hydride reduction (or LAH reduction followed by PCC oxidation) of the resulting diesters then provided the desired pimelaldehydes 1 in acceptable overall yields.
62. See for example: a) M. Bertau, M. Bürli, E. Hungerbühler, P. Wagner, Tetrahedron: Asymmetry 2001, 12, 2103-2107;
63. b) V. Spiliotis, D. Papahatjis, N. Ragoussis, Tetrahedron Lett. 1990, 31, 1615-1616.
64. Alternative highly efficient and enantioselective ruthenium-catalyzed β-keto ester reductions can be diastereounselective: a) R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856-5858; b) M. Kitamura, T. Ohkuma, M. Tokunaga, R. Noyori, Tetrahedron: Asymmetry 1990, 1, 1-4; c) J. P. Genêt, X. Pfister, V. Ratovelomanana-Vidal, C. Pinel, J. A. Laffitte, Tetrahedron Lett. 1994, 35, 4559-4562.
65. Alternative highly efficient and enantioselective ruthenium-catalyzed β-keto ester reductions can be diastereounselective: a) R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856-5858; b) M. Kitamura, T. Ohkuma, M. Tokunaga, R. Noyori, Tetrahedron: Asymmetry 1990, 1, 1-4; c) J. P. Genêt, X. Pfister, V. Ratovelomanana-Vidal, C. Pinel, J. A. Laffitte, Tetrahedron Lett. 1994, 35, 4559-4562.
66. Alternative highly efficient and enantioselective ruthenium-catalyzed β-keto ester reductions can be diastereounselective: a) R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856-5858; b) M. Kitamura, T. Ohkuma, M. Tokunaga, R. Noyori, Tetrahedron: Asymmetry 1990, 1, 1-4; c) J. P. Genêt, X. Pfister, V. Ratovelomanana-Vidal, C. Pinel, J. A. Laffitte, Tetrahedron Lett. 1994, 35, 4559-4562.
67. 13C NMR spectra, as well as high-resolution mass spectroscopic analysis.