Catalytic, asymmetric alkylation of imines

Tetrahedron

Volumn 63, Issue 39, 2007, Pages 9581-9597

  Ferraris, Dana ^a  

^a MGI Pharma   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKALOID; BETA LACTAM ANTIBIOTIC; EMETINE; IMINE; KETENE DERIVATIVE; PIPERIDINE DERIVATIVE; SEDAMINE; SILANE; TUBULOSINE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ARYLATION; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; DRUG SYNTHESIS; MANNICH REACTION; MOLECULAR INTERACTION; MOLECULAR MECHANICS; PRIORITY JOURNAL; RESPIRATORY TRACT DISEASE; REVIEW; STAUDINGER REACTION; STEREOCHEMISTRY;

EID: 34547796504     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.06.043     Document Type: Review

References (81)

1. In: Ojima I. (Ed). Catalytic, Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York, NY 493-542 Chapter 8B
2. Mengel A., and Reiser O. Chem. Rev. 99 (1999) 1191
3. Heintzelman G.R., Weinreb S.M., and Parvez M. J. Org. Chem. 61 (1996) 4594
4. Baillarge M., and Goffic F.L. Synth. Commun. 17 (1987) 1603
5. Weinreb S.M., and Orr R.K. Synthesis (2005) 1205
6. Taggi A.E., Hafez A.M., and Lectka T. Acc. Chem. Res. 36 (2003) 10
7. Panunzio M., and Zarantonello P. Org. Process Res. Dev. 2 (1998) 49
8. Yamanaka M., Itoh J., Fuchibe K., and Akiyama T. J. Am. Chem. Soc. 129 (2007) 6756
9. France S., Wack H., Hafez A., Taggi A.E., Witsil D.R., and Lectka T. Org. Lett. 4 (2002) 1603
10. France S., Shah M.H., Weatherwax A., Wack H., Roth J.P., and Lectka T. J. Am. Chem. Soc. 127 (2005) 1206
11. Vachal P., and Jacobsen E.N. Org. Lett. 6 (2000) 867
12. Vachal P., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 10012
13. Enders D., and Reinhold U. Tetrahedron: Asymmetry 8 (1997) 1895
14. Kobayashi S., and Ishitani H. Chem. Rev. 99 (1999) 1069
15. Edwards M.L., Matt J.E., Wenstrup D.L., Kemper C.A., Persichetti R.A., and Margolin A.L. Org. Prep. Proced. Int. 28 (1996) 193
16. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), Wiley, New York, NY p 609
17. Ferraris D., Young B., Dudding T., Drury III W.J., and Lectka T. Tetrahedron 55 (1999) 8869
18. Love B.E., Raje P.S., and Williams II T.C. Synlett (1994) 493
19. Krzyzanowska B., and Stec W.J. Synthesis (1982) 270
20. Desrosiers J.-N., Cote A., Boezio A.A., and Charette A.B. Org. Synth. 83 (2006) 5
21. Chiacchio U., Corsaro A., Compagnini A., and Giovanni P. J. Chem. Soc., Perkin Trans. 1 (1983) 671
22. Uraguchi D., Sorimachi K., and Terada M. J. Am. Chem. Soc. 127 (2005) 9360
23. Kupfer R., Meier S., and Wuerthwein E.-U. Synthesis 8 (1984) 688
24. Muenser P., and Steglich W. Synthesis 11 (1987) 223
25. Hafez A.M., Taggi A.E., Dudding T., and Lectka T. J. Am. Chem. Soc. 123 (2001) 10853
26. Boger D.L., and Myers Jr. J.B. J. Org. Chem. 56 (1991) 5385
27. Barluenga J., Joglar J., Gonzales F.J., and Fustero S. Synlett (1990) 129
28. Sieber J.D., and Morken J.P. J. Am. Chem. Soc. 128 (2006) 74
29. Bradley D.C., and Chisolm M.H. Acc. Chem. Res. 9 (1976) 273
30. Hart D.J., Kanai K., Thomas D.G., and Yang T.-K. J. Org. Chem. 48 (1983) 289
31. Cainelli G., Giacomini D., Galletti P., and Gaiba A. Synlett (1996) 657
32. Colvin E.W., McGarry D., and Nugent M.J. Tetrahedron 44 (1988) 4157
33. Consequently, the electron-rich methoxyphenyl group can be removed via ceric ammonium nitrate (CAN) after the alkylation in reasonable yields. See Ref. 11.
34. Manhas M.S., Ghosh M., and Bose A.K. J. Org. Chem. 55 (1990) 575
35. Danheiser R.L., Okamoto I., Lawlor M.D., and Lee T.W. Org. Synth. 80 (2003) 160
36. Tietze L.F., and Bratz M. Synthesis (1989) 439
37. Josephsohn N.S., Snapper M.L., and Hoveyda A.H. J. Am. Chem. Soc. 126 (2004) 3734
38. For early attempts at catalytic addition of organolithium reagents to imines see:
39. Tomioka K., Inoue I., Shindo M., and Koga K. Tetrahedron Lett. 32 (1991) 3095
40. Denmark S.E., Nakajima N., and Nicaise O.J.-C. J. Am. Chem. Soc. 116 (1994) 8797
41. Fujieda H., Kanai M., Kambara T., Iida A., and Tomioka K. J. Am. Chem. Soc. 119 (1997) 2060
42. In: Morrison J.D. (Ed). Asymmetric Synthesis Vol. 3 (1984), Academic, New York, NY Chapters 1 and 2
43. Ishitani H., Ueno M., and Kobayashi S. J. Am. Chem. Soc. 119 (1997) 7153
44. Josephsohn N.S., Carswell E.L., Snapper M.L., and Hoveyda A.H. Org. Lett. 7 (2005) 2711
45. Taggi A., Hafez A., Wack H., Young B., Ferraris D., and Lectka T. J. Am. Chem. Soc. 124 (2002) 6626
46. Ferraris D., Young B., Dudding T., and Lectka T. J. Am. Chem. Soc. 120 (1998) 4548
47. Ferraris D., Young B., Cox C., Drury W.J., Dudding T., and Lectka T. J. Org. Chem. 63 (1998) 6090
48. Ferraris D., Dudding T., Young B., Drury III W.J., and Lectka T. J. Org. Chem. 64 (1999) 2168
49. Ferraris D., Young B., Cox C., Dudding T., Drury W.J., Ryzhkov L., Taggi A., and Lectka T. J. Am. Chem. Soc. 124 (2002) 67
50. Hagiwara E., Fujii A., and Sodeoka M. J. Am. Chem. Soc. 120 (1998) 2474
51. Josephsohn N.S., Snapper M.L., and Hoveyda A.H. J. Am. Chem. Soc. 125 (2003) 4018
52. Pu L., and Yu H.-B. Chem. Rev. 101 (2001) 757
53. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763
54. Fujihara H., Nagai K., and Tomioka K. J. Am. Chem. Soc. 122 (2000) 12055
55. Soeta T., Nagai K., Fujihara H., Kuriyama M., and Tomioka K. J. Org. Chem. 68 (2003) 9723
56. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 984
57. Traverse J.F., Hoveyda A.H., and Snapper M.L. Org. Lett. 5 (2003) 3273
58. Porter J.R., Traverse J.F., Hoveyda A.H., and Snapper M.L. J. Am. Chem. Soc. 123 (2001) 10409
59. Lauzon C., and Charette A.B. Org. Lett. 8 (2006) 2743
60. Uozumi Y., Suzuki N., Ogiwara A., and Hayashi T. Tetrahedron 50 (1994) 4293
61. Hayashi T., and Ishigedani M. J. Am. Chem. Soc. 122 (2000) 976
62. Spencer C.M., Foulds D., and Peters D.H. Drugs 46 (1993) 1055
63. Hassan J., Sevignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359
64. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
65. Tokunaga N., Otomaru K., Ueyama K., Shintani R., and Hayashi T. J. Am. Chem. Soc. 126 (2004) 13584
66. Otomaru Y., Tokunaga N., Shintani R., and Hayashi T. Org. Lett. 7 (2005) 307
67. Yet L. Angew. Chem., Int. Ed. 40 (2001) 875
68. Masumoto S., Usuda H., Suzuki M., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 5634
69. Fernandes R.A., and Yamamoto Y. J. Org. Chem. 69 (2004) 735
70. Evans D.A., Burgey C.S., Paras N.A., Vojkovsky T., and Tregay S.W. J. Am. Chem. Soc. 120 (1998) 5824
71. Drury III W.J., Ferraris D., Cox C., Young B., and Lectka T. J. Am. Chem. Soc. 120 (1998) 11006
72. Mennen S.M., Gipson J.D., Kim Y.R., and Miller S.J. J. Am. Chem. Soc. 127 (2005) 1654
73. Rolinson G.N. J. Antimicrob. Chemother. 41 (1998) 589
74. Plotkin M.J., and Shnayerson M. The Killers Within: The Deadly Rise of Drug Resistant Bacteria. 1st ed. (2002), Little, Brown, New York, NY
75. Compere D., Marazano C., and Das B.C. J. Org. Chem. 64 (1999) 4528
76. Poerwono H., Higashiyama K., and Takahashi H. Heterocycles 47 (1998) 262
77. Yu C.Y., and Meth-Cohn O. Tetrahedron Lett. 40 (1999) 6665
78. Ito A., Lee Y.-H., Chai M.P., Gupta N.R., Farnsforth N.R., Gordell G.A., Pezzuto J.M., and Kinghorn A.D. J. Nat. Prod. 62 (1999) 1346
79. Gonzales-Garza M.T., Martlin S.A., Mata-Cardena B.D., and Said-Fernandez S. J. Pharm. Pharmacol. 45 (1993) 144
80. Itoh T., Miyazaki M., Fukuoka H., Nagata K., and Ohsawa A. Org. Lett. 8 (2006) 1295
81. Tietze L.F., Rackelmann N., and Muller I. Chem.-Eur. J. 10 (2004) 2772