Borane-mediated aldol cycloreduction of monoenone monoketones: Diastereoselective formation of quaternary centers

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 11-14

  Huddleston, Ryan R ^a   Cauble, David F ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MONOENONE MONOKETONES;

REDUCTION; SALTS;

KETONES;

BORANE DERIVATIVE; KETONE DERIVATIVE; RHODIUM;

ALDOL REACTION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ENVIRONMENTAL TEMPERATURE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; X RAY DIFFRACTION;

BORANES; CATALYSIS; CYCLIZATION; HYDROCARBONS, CYCLIC; KETONES; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RHODIUM; STEREOISOMERISM; TEMPERATURE;

EID: 0037428016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020629f     Document Type: Article

References (37)

1. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H., Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), ed. E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
2. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H., Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), ed. E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
3. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H., Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), ed. E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
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5. For selected reviews on catalytic enantioselective aldol reactions, see: (a) Machajewski, T. D.; Wong, C.-H., Lerner, R. A. Angew. Chem., Int. Ed. 2000, 39, 1352. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432. (c) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. III, p 1. (e) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl), ed. E21; Helmchen, G., Hoffman, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3, p 1730.
6. Aldol cyclizations have been catalyzed by antibodies and chiral amines: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. Org. Lett. 1999, 1, 59. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (d) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358. (e) Eder, U.; Weichert, R.; Sauer, G. German Patent DE 2014757, Oct. 7, 1971.
7. Aldol cyclizations have been catalyzed by antibodies and chiral amines: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. Org. Lett. 1999, 1, 59. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (d) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358. (e) Eder, U.; Weichert, R.; Sauer, G. German Patent DE 2014757, Oct. 7, 1971.
8. Aldol cyclizations have been catalyzed by antibodies and chiral amines: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. Org. Lett. 1999, 1, 59. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (d) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358. (e) Eder, U.; Weichert, R.; Sauer, G. German Patent DE 2014757, Oct. 7, 1971.
9. Aldol cyclizations have been catalyzed by antibodies and chiral amines: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. Org. Lett. 1999, 1, 59. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (d) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358. (e) Eder, U.; Weichert, R.; Sauer, G. German Patent DE 2014757, Oct. 7, 1971.
10. Aldol cyclizations have been catalyzed by antibodies and chiral amines: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. Org. Lett. 1999, 1, 59. (b) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496. (c) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615. (d) Agami, C.; Platzer, N.; Sevestre, H. Bull. Soc. Chim. Fr. 1987, 2, 358. (e) Eder, U.; Weichert, R.; Sauer, G. German Patent DE 2014757, Oct. 7, 1971.
11. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
12. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
13. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
14. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
15. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
16. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
17. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
18. For catalytic reductive aldol processes, see: (a) Revis, A.; Hilty, T. K. Tetrahedron Lett. 1987, 28, 4809. (b) Matsuda, I.; Takahashi, K.; Sato, S. Tetrahedron Lett. 1990, 31, 5331. (c) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 2005. (d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237. (e) Ooi, T.; Doda, K.; Sakai, D.; Maruoka, K. Tetrahedron Lett. 1999, 40, 2133. (f) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. (g) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528. (h) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Org. Lett. 2001, 3, 1829.
19. For a review, see: Huddleston, R. R.; Krische, M. J. Synlett 2002, in press.
20. Baik, T.-G.; Luiz, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. A nonstereoselective catalytic aldol cycloreduction was subsequently reported: Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
21. Baik, T.-G.; Luiz, A. L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. A nonstereoselective catalytic aldol cycloreduction was subsequently reported: Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Synlett 2001, 1302.
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27. For selected reviews on boron enolates, see: (a) Paterson, I.; Doughty, V. A.; Florence, G.; Gerlach, K.; McLeod, M. D.; Scott, J. P.; Trieselmann, T. ACS Symposium Series 783; American Chemical Society: Washington, DC, 2001; p 195. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (c) Gennari, C. Pure Appl. Chem. 1997, 69, 507. (d) Paterson, I. Chem. Ind. 1988, 12, 390. (e) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
28. For selected reviews on boron enolates, see: (a) Paterson, I.; Doughty, V. A.; Florence, G.; Gerlach, K.; McLeod, M. D.; Scott, J. P.; Trieselmann, T. ACS Symposium Series 783; American Chemical Society: Washington, DC, 2001; p 195. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1. (c) Gennari, C. Pure Appl. Chem. 1997, 69, 507. (d) Paterson, I. Chem. Ind. 1988, 12, 390. (e) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
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33. 2, and triphenylphosphine (30.4 mmol, 100 mol %) was added; the reaction mixture was allowed to stir for 2 h at 25°C. At this point, the appropriate Wittig reagent (30.4 mmol, 100 mol %) was added in portions over 10 min and the solution stirred for 18 h. The residue was evaporated onto silica and subjected to column chromatography to afford monoenone monoketones 1a-5a.
34. 2 (200 mL, 0.091 M), and the acetophenone-derived Wittig reagent (18.2 mmol, 100 mol %) was added in portions over 10 min; the solution was allowed to stir for 18 h. The residue was evaporated onto silica and subjected to column chromatography to afford the monoenone monoketone 6a (4.75 g, 86% yield) as a clear colorless oil.
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36. See Supporting Information for crystallographic data.
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