Highly diastereoselective addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl aldimines: A practical and general access to chiral α-branched amines

Journal of Organic Chemistry

Volumn 75, Issue 3, 2010, Pages 941-944

  Chen, Bai Ling ^a   Wang, Bing ^a   Lin, Guo Qiang ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; ASYMMETRIC SYNTHESIS; CHEMICAL EQUATIONS; DIASTEREO-SELECTIVITY; DIASTEREOSELECTIVE ADDITIONS; OPTICAL PURITY; REACTION PARTNERS; SYNTHETIC TRANSFORMATIONS;

ACETYLENE; AMINES; CHLORINE COMPOUNDS; COMPLEXATION; STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ALKYNYLMAGNESIUM CHLORIDE; AMINE; ANGUSTUREINE; CUSPAREINE; MAGNESIUM CHLORIDE; N BUTANESULFINYL ALDIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PROTEIN PURIFICATION; STEREOCHEMISTRY; SYNTHESIS;

ALKYNES; AMINES; IMINES; MAGNESIUM CHLORIDE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 75749144634     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902424m     Document Type: Article

References (76)

1. For addition of carbanions, see: (a) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913.
2. (b) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron 1999, 55, 8883.
3. (c) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268.
4. (d) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772.
5. (e) Evans, J. W.; Ellman, J. A. J. Org. Chem. 2003, 68, 9948.
6. (f) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589.
7. (g) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847.
8. For addition of enolates, see: (a) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
9. (b) Tang, T. P.; Ellman, J. A. J. Org. Chem. 2002, 67, 7819.
10. (c) Reference 1e.
11. (d) Wang, Y.; He, Q.-F.; Wang, H.-W.; Zhou, X.; Huang, Z.-Y.; Qin, Y. J. Org. Chem. 2006, 71, 1588.
12. For additions of organoboron species, see: (a) Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092.
13. (b) Dai, H.; Lu, X. Org. Lett. 2007, 9, 3077.
14. (c) Bennen, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6910.
15. (d) Brak, K.; Ellman, J. A. J. Am. Chem. Soc. 2009, 131, 3850.
16. For reduction of ketimines, see: (a) Borg, G.; Cogan, D. A.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709.
17. (b) Colyer, J. T.; Andersen, N. G.; Tedrow, J. S.; Soukup, T. S.; Faul, M. M. J. Org. Chem. 2006, 71, 6859.
18. For reviews, see: (a) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
19. (b) Lin, G.-Q.; Xu, M.-H.; Zhong, Y.-W.; Sun, X.-W. Acc. Chem. Res. 2008, 41, 831.
20. (c) Ferreira, F.; Botuha, C.; Chemla, F.; Pérez-Luna, A. Chem. Soc. Rev. 2009, 38, 1162.
21. (d) Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869.
22. (e) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13.
23. Selected synthetic approaches to chiral propargylic amines: (a) Huffman, M. A.; Yasuda, N.; DeCamp, A. E.; Grabowski, E. J. J. J. Org. Chem. 1995, 60, 1590.
24. (b) Fischer, C.; Carreira, E. M. Org. Lett. 2001, 3, 4319.
25. (c) Li, C.-J.; Wei, C. Chem. Commun. 2002, 268.
26. (d) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5638.
27. (e) Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. Org. Lett. 2003, 5, 3273.
28. (f) Fischer, C.; Carreira, E. M. Org. Lett. 2004, 6, 1497.
29. (g) Wei, C.; Mague, J. T.; Li, C.-J. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5749.
30. (h) Gommermann, N.; Knochel, P. Chem. Commun. 2004, 2324.
31. (i) Turcaud, S.; Berhal, F.; Royer, J. J. Org. Chem. 2007, 72, 7893.
32. (j) Bishop, J. A.; Lou, S.; Schaus, S. E. Angew. Chem., Int. Ed. 2009, 48, 4337. For reviews, see:
33. (k) Wei, C.; Li, Z.; Li, C.-J. Synlett 2004, 1472.
34. (l) Reginato, R.; Meffre, P.; Gaggini, F. Amino Acids 2005, 29, 81.
35. (m) Zani, L.; Bolm, C. Chem. Commun. 2006, 4263.
36. (n) Trost, B. M.; Weiss, A. H. Adv. Synth. Catal. 2009, 351, 963.
37. For recent applications, see: (a) Cantel, S.; Isaad, A. L. C.; Scrima, M.; Levy, J. J.; DiMarchi, R. D.; Rovero, P.; Helperin, J. A.; D'Ursi, A. M.; Papini, A. M.; Chorev, M. J. Org. Chem. 2008, 73, 5663.
38. (b) Lo, V. K.-Y.; Zhou, C.-Y.; Wong, M.-K.; Che, C.-M. Chem. Commun. 2010, 46, 213. For a review on click chemistry, see:
39. (c) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
40. Addition of alkynyllithium: (a) Patterson, A. W.; Ellman, J. A. J. Org. Chem. 2006, 71, 7110 (ketimines).
41. (b) Ding, C.-H.; Chen, D.-D.; Luo, Z.-B.; Dai, L.-X.; Hou, X.-L. Synlett 2006, 1272 (addition to racemic substrates, 88-95% de).
42. (c) Chen, X.-Y.; Qiu, X.-L.; Qing, F.-L. Tetrahedron 2008, 64, 2301 (trifluoromethylacetylide, 72-98% de). Hypervalent silicon species:
43. (d) Letten, R. B., II; Scheidt, K. A. Org. Lett. 2005, 7, 3227 (one example, 90% de). Alkynylcerium reagent:
44. (e) Hodgson, D. M.; Kloesges, J.; Evans, B. Org. Lett. 2008, 10, 2781 (one example, 70% de). Widely variable diastereoselectivities were obtained in previous reports using alkynylmagnesium bromide:
45. (f) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051 (one example, 54% de).
46. (g) Reference 1d (one example, 80% de).
47. (h) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641 (one example, 90% de).
48. (a) Wang, B.; Wang, Y.-J. Org. Lett. 2009, 11, 3410.
49. (b) Wang, B.; Liu, R.-H. Eur. J. Org. Chem. 2009, 2845.
50. (c) Liu, R.-H.; Fang, K.; Wang, B.; Xu, M.-H.; Lin, G.-Q. J. Org. Chem. 2008, 73, 3307.
51. Asymmetric hydrogenation leading to 2-substituted tetrahydroquinolines: (a) Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536.
52. (b) Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2006, 45, 2260.
53. (c) Wang, X.-B.; Zhou, Y.-G. J. Org. Chem. 2008, 73, 5640.
54. (d) Wang, X.-B.; Wang, D.-W.; Lu, S.-M.; Yu, C.-B.; Zhou, Y.-G. Tetrahedron: Asymmetry 2009, 20, 1040.
55. (e) Wang, D.-W.; Wang, X.-B.; Lu, S.-M.; Yu, C.-B.; Zhou, Y.-G. J. Org. Chem. 2009, 74, 2780.
56. (f) Wang, C.; Li, C.; Wu, X.; Pettman, A.; Xiao, J. Angew. Chem., Int. Ed. 2009, 48, 6524.
57. (g) Tadaoka, H.; Cartigny, D.; Nagano, T.; Gosavi, T.; Ayad, T.; Genêt, J.-P.; Ohshima, T.; Ratovelomanana-Vidal, V.; Mashima, K. Chem. - Eur. J. 2009, 15, 9990. For an excellent review, see:
58. (h) Zhou, Y.-G. Acc. Chem. Res. 2007, 40, 1357.
59. Isolation of angustureine: (a) Jacquemond-Collet, I.; Hannedouche, S.; Fabre, N.; Fourasté, I.; Moulis, C. Phytochemistry 1999, 51, 1167. Asymmetric synthesis of 7:
60. (b) References 10a and 10b.
61. (c) Theeraladanon, C.; Arisawa, M.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2005, 16, 827.
62. (d) Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45, 3683.
63. (e) Wang, Z.-J.; Zhou, H.-F.; Wang, T.-L.; He, Y.-M.; Fan, Q.-H. Green Chem. 2009, 11, 767. Synthesis of racemic 7:
64. (f) Shahane, S.; Louafi, F.; Moreau, J.; Hurvois, J.-P.; Renaud, J.-L.; van der Weghe, P.; Roisnel, T. Eur. J. Org. Chem. 2008, 4622.
65. (g) O'Byrne, A.; Evans, P. Tetrahedron 2008, 64, 8067.
66. (h) Kothandaraman, P.; Foo, S. J.; Chan, P. W. H. J. Org. Chem. 2009, 74, 5947.
67. (i) Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2007, 72, 6577.
68. (j) Avemaria, F.; Vanderheiden, S.; Bräse, S. Tetrahedron 2003, 59, 6785.
69. Isolation of cuspareine: (a) Rakotoson, J. H.; Fabre, N.; Jacquemond-Collet, I.; Hannedouche, S.; Fourasté, I.; Moulis, C. Planta Med. 1998, 64, 762. Asymmetric synthesis of 10:
70. (b) References 10a, 10b, and 11d. Synthesis of racemic 10:
71. (d) References 11f and 11g.
72. For reviews on the Buchwald-Hartwig amination, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
73. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
74. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
75. (d) Buchwald, S. L.; Muci, A. Top. Curr. Chem. 2002, 219, 133.
76. Fang, Z.; Song, Y.; Sarkar, T.; Hamel, E.; Fogler, W. E.; Agoston, G. E.; Fanwick, P. E.; Cushman, M. J. Org. Chem. 2008, 73, 4241.