Silyl fluoride electrophiles for the enantioselective synthesis of silylated pyrrolidine catalysts

Journal of Organic Chemistry

Volumn 76, Issue 17, 2011, Pages 7065-7075

  Jentzsch, Kaleb I ^a   Min, Taewoo ^a   Etcheson, Jennifer I ^a   Fettinger, James C ^a   Franz, Annaliese K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADINGS; ELECTROPHILES; ENANTIOSELECTIVE SYNTHESIS; ESI MASS SPECTROMETRY; HIGH YIELD; HYDROGEN BONDINGS; LITHIATION; MICHAEL REACTIONS; NITRO ACCEPTORS; NITROOLEFINS; PYRROLIDINES; SIDE REACTIONS;

ALDEHYDES; CHEMICAL ACTIVATION; ENANTIOSELECTIVITY; HYDROGEN; MASS SPECTROMETRY; OLEFINS; ORGANIC COMPOUNDS; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL);

CATALYSTS;

ACETALDEHYDE; ALKENE; AMINE; ELECTROPHILE; PROPIONALDEHYDE; PYRROLIDINE DERIVATIVE; SILYL FLUORIDE ELECTROPHILE; SILYLATED PYRROLIDINE; SPARTEINE; TERT BUTYLDIPHENYLSILYLPYRROLIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; HYDROGEN BOND; LITHIATION; MICHAEL ADDITION; REACTION ANALYSIS; SYNTHESIS;

CATALYSIS; FLUORIDES; MOLECULAR STRUCTURE; PYRROLIDINES; SILANES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM;

EID: 80052159472     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200991q     Document Type: Article

References (70)

1. MacMillan, D. W. C. Nature 2008, 455, 304
2. Rueping, M.; Merino, E.; Sugiono, E. Adv. Synth. Catal. 2008, 350, 2127
3. Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861
4. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis-From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2005.
5. Xu, L.-W.; Li, L.; Shi, Z.-H. Adv. Synth. Catal. 2010, 352, 243
6. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; John Wiley & Sons: Hamilton, Ontario, 2000.
7. Lipshutz, B. H.; Hungate, R. W. J. Org. Chem. 1981, 46, 1410
8. Block, E.; Aslam, M. J. Am. Chem. Soc. 1985, 107, 6729
9. Terao, J.; Kambe, N. Chem. Rec. 2007, 7, 57
10. Bartoszewicz, A.; Kalek, M.; Nilsson, J.; Hiresova, R.; Stawinski, J. Synlett 2008, 2008, 37
11. Eaborn, C. J. Chem. Soc. 1952, 2840
12. Hayashi, Y.; Gotoh, H.; Hayashi, T.; Shoji, M. Angew. Chem., Int. Ed. 2005, 44, 4212
13. Gotoh, H.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2007, 9, 5307
14. List, B. Synlett 2001, 2001, 1675
15. Shi, Z.-H.; Sheng, H.; Yang, K.-F.; Jiang, J.-X.; Lai, G.-Q.; Lu, Y.; Xu, L. W. Eur. J. Org. Chem. 2011, 66
16. Zheng, Z.; Perkins, B. L.; Ni, B. J. Am. Chem. Soc. 2009, 132, 50
17. Patil, M. P.; Sharma, A. K.; Sunoj, R. B. J. Org. Chem. 2010, 75, 7310
18. Min, T.; Jentzsch, K.; Franz, A. K.; Etcheson, J. Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, Mar 21-25, 2010; American Chemical Society: Washington, DC, 2010; ORGN-201.
19. Husmann, R.; JoCrres, M.; Raabe, G.; Bolm, C. Chem. - Eur. J. 2010, 16, 12549
20. Bauer, J. O.; Stiller, J.; MarqueNs-López, E.; Strohfeldt, K.; Christmann, M.; Strohmann, C. Chem. - Eur. J. 2010, 16, 12553
21. An example of a catalytic asymmetric hydrosilylation has been reported where higher enantioselectivity is observed using a silyl fluoride substrate compared to a silyl chloride substrate; see: Hatanaka, Y.; Goda, K.-I.; Yamashita, F.; Hiyama, T. Tetrahedron Lett. 1994, 35, 7981
22. Sieburth, S. M.; Chen, C.-A. Eur. J. Org. Chem. 2006, 311
23. Tacke, R.; Schmid, T.; Penka, M.; Burschka, C.; Bains, W.; Warneck, J. Organometallics 2004, 23, 4915
24. Mortensen, M.; Husmann, R.; Veri, E.; Bolm, C. Chem. Soc. Rev. 2009, 38, 1002
25. Damrauer, R.; Simon, R. A.; Kanner, B. Organometallics 1988, 7, 1161
26. Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552
27. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231
28. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708
29. Wiberg, K. B.; Bailey, W. F. J. Am. Chem. Soc. 2001, 123, 8231
30. Weisenburger, G. A.; Faibish, N. C.; Pippel, D. J.; Beak, P. J. Am. Chem. Soc. 1999, 121, 9522
31. Basu, A.; Thayumanavan, S. Angew. Chem., Int. Ed. 2002, 41, 716
32. Tenenbaum, J. M.; Woerpel, K. A. Org. Lett. 2003, 5, 4325
33. Jones, P. R.; Cheng, A. H. B.; Albanesi, T. E. Organometallics 1984, 3, 78
34. Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1989, 54, 268
35. Stead, D.; Carbone, G.; O'Brien, P.; Campos, K. R.; Coldham, I.; Sanderson, A. J. Am. Chem. Soc. 2010, 132, 7260
36. Kaul, R.; Brouillette, Y.; Sajjadi, Z.; Hansford, K. A.; Lubell, W. D. J. Org. Chem. 2004, 69, 6131
37. Srinivasan, N.; Yurek-George, A.; Ganesan, A. Mol. Diversity 2005, 9, 291
38. Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870
39. Stead, D.; O'Brien, P.; Sanderson, A. Org. Lett. 2008, 10, 1409
40. Cartledge, F. K. Organometallics 1983, 2, 425
41. Shimizu, N.; Takesue, N.; Yamamoto, A.; Tsutsumi, T.; Yasuhara, S.; Tsuno, Y. Chem. Lett. 1992, 1263
42. Golubev, O.; Panov, D.; Ploom, A.; Tuulmets, A.; Nguyen, B. T. J. Organomet. Chem. 2007, 692, 3700
43. Ploom, A.; Tuulmets, A.; Järv, J. Phosphorus, Sulfur, Silicon Relat. Elem. 2010, 185, 2503
44. Mayr, H.; Pock, R. Tetrahedron 1986, 42, 4211
45. Lambert, J. B.; Zhao, Y.; Emblidge, R. W.; Salvador, L. A.; Liu, X.; So, J.-H.; Chelius, E. C. Acc. Chem. Res. 1998, 32, 183
46. Brook, M. A.; Neuy, A. J. Org. Chem. 1990, 55, 3609
47. Hut'ka, M.; Poláková, V.; Marák, J.; Kaniansky, D.; Šebesta, R.; Toma, Š. Eur. J. Org. Chem. 2010, 6430
48. Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559
49. Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172
50. Mase, N.; Thayumanavan, R.; Tanaka, F.; Barbas, C. F. Org. Lett. 2004, 6, 2527
51. Transition-state calculations performed using Gaussian with the B3LYP/6-31G(d) level of theory indicates that the syn -addition is preferred over anti -addition for all three silyl pyrrolidine catalysts in the gas phase; see the Supporting Information and: Zhao, J.-Q.; Gan, L.-H. Eur. J. Org. Chem. 2009, 2009, 2661
52. Wang, J.; Li, H.; Lou, B.; Zu, L.; Guo, H.; Wang, W. Chem.A - Eur. J. 2006, 12, 4321
53. Patil, M. P.; Sunoj, R. B. Chem.- - Eur. J. 2008, 14, 10472
54. García-García, P.; Ladépêche, A.; Halder, R.; List, B. Angew. Chem., Int. Ed. 2008, 47, 4719
55. Hayashi, Y.; Itoh, T.; Ohkubo, M.; Ishikawa, H. Angew. Chem., Int. Ed. 2008, 47, 4722
56. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
57. Patora-Komisarska, K.; Benohoud, M.; Ishikawa, H.; Seebach, D.; Hayashi, Y. Helv. Chim. Acta 2011, 94, 719
58. Wu, Z.-J.; Luo, S.-W.; Xie, J.-W.; Xu, X.-Y.; Fang, D.-M.; Zhang, G.-L. J. Am. Soc. Mass. Spectrom. 2007, 18, 2074
59. Marquez, C.; Metzger, J. O. Chem. Commun. 2006, 1539
60. Li, B.-L.; Wang, Y.-F.; Luo, S.-P.; Zhong, A.-G.; Li, Z.-B.; Du, X.-H.; Xu, D.-Q. Eur. J. Org. Chem. 2010, 656
61. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119
62. Zhang, Z.-H.; Dong, X.-Q.; Chen, D.; Wang, C.-J. Chem.h - Eur. J. 2008, 14, 8780
63. Miyashita, M.; Yanami, T.; Kumazawa, T.; Yoshikoshi, A. J. Am. Chem. Soc. 1984, 106, 2149
64. Boarino, L.; Geobaldo, F.; Borini, S.; Rossi, A. M.; Rivolo, P.; Rocchia, M.; Garrone, E.; Amato, G. Phys. Rev. B 2001, 64, 205308
65. Yadav, J. S.; Reddy, A. R.; Rao, Y. G.; Narsaiah, A. V.; Reddy, B. V. S. Synthesis 2007, 2007, 3447
66. Betancort, J. M.; Barbas, C. F. Org. Lett. 2001, 3, 3737
67. Wang, W.; Wang, J.; Li, H. Angew. Chem., Int. Ed. 2005, 44, 1369
68. Kotrusz, P. Toma, S.; Schmalz, H.-G.; Adler, A. Eur. J. Org. Chem. 2004, 1577
69. Luo, R.-S.; Weng, J.; Ai, H.-B.; Lu, G.; Chan, A. S. C. Adv. Synth. Catal. 2009, 351, 2449
70. Andrey, O.; Alexakis, A.; Tomassini, A.; Bernardinelli, G. Adv. Synth. Catal. 2004, 346, 1147