Cyclization of zincated α-N-homoallylamino nitriles: A new entry to enantiopure 2,3-methanopyrrolidines

Chemistry - A European Journal

Volumn 16, Issue 42, 2010, Pages 12668-12677

  Ouizem, Sabrina ^a   Cheramy, Sandrine ^a   Botuha, Candice ^a   Chemla, Fabrice ^a   Ferreira, Franck ^a   Pérez Luna, Alejandro ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

cyclization; enantioselectivity; metalation; sigmatropic rearrangement; ylides

Indexed keywords

AMINO NITRILES; AZA-COPE REARRANGEMENT; CONFIGURATIONALLY; CYCLOADDITION REACTION; ENANTIOPURE; GOOD YIELD; HOMOALLYLIC AMINES; LITHIUM DIISOPROPYLAMIDE; METALATIONS; SIGMATROPIC REARRANGEMENTS; STEREOGENIC CENTERS; STEREOSELECTIVE CYCLIZATIONS; STEREOSPECIFIC; TRANSMETALATION; YLIDES; ZINC BROMIDE;

AMINATION; BROMINE COMPOUNDS; CYANIDES; CYCLOADDITION; ENANTIOSELECTIVITY; LITHIUM; SULFUR COMPOUNDS; ZINC;

CYCLIZATION;

EID: 78249279978     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001639     Document Type: Article

References (114)

1. T. Opatz, Synthesis 2009, 1941 - 1960.
2. Selected reviews
3. J. D. Albright, Tetrahedron 1983, 39, 3207 - 3233
4. H.-P. Husson, J. Royer, Chem. Soc. Rev. 1999, 28, 383 - 394
5. D. Enders, J. P. Shilvock, Chem. Soc. Rev. 2000, 29, 359 - 373.
6. For leading references, see:, D. Enders, J. Kirchhoff, P. Gerdes, D. Mannes, G. Raabe, J. Runsink, G. Boche, M. Marsch, H. Ahlbrecht, H. Sommer, Eur. J. Org. Chem. 1998, 63 - 72, and references therein.
7. An example of addition of a zincated dibenzylaminoacetonitrile to an aldehyde has been reported, see:, E. Leclerc, E. Vrancken, P. Mangeney, J. Org. Chem. 2002, 67, 8928 - 8937.
8. 2 has been reported, see:, R. M. Jacobson, J. W. Clader, Tetrahedron Lett. 1980, 21, 1205 - 1208.
9. A. Jonczyk, D. Lipiak, T. Zdrojewski, Tetrahedron 1990, 46, 1025 - 1038
10. T. Zdrojewski, A. Jonczyk, Synthesis 1990, 224 - 233
11. T. Zdrojewski, A. Jonczyk, Liebigs Ann. Chem. 1993, 375 - 378
12. A. Jonczyk, Z. Pakulski, Tetrahedron Lett. 1996, 37, 8909 - 8912.
13. J.-L. Wang, C.-H. Ueng, M.-C. P. Yeh, Tetrahedron Lett. 1995, 36, 2823 - 2826.
14. A. Pérez-Luna, C. Botuha, F. Ferreira, F. Chemla, New J. Chem. 2008, 32, 594 - 606.
15. E. Lorthiois, I. Marek, J.-F. Normant, Tetrahedron Lett. 1997, 38, 89 - 92.
16. P. Karoyan, G. Chassaing, Tetrahedron Lett. 1997, 38, 85 - 88.
17. E. Lorthiois, I. Marek, J.-F. Normant, J. Org. Chem. 1998, 63, 2442 - 2450.
18. S. Hanessian, L. Azzas, Acc. Chem. Res. 2008, 41, 1241 - 1251, and references therein.
19. E. Le Gall, C. Gosmini, M. Troupel, Tetrahedron Lett. 2006, 47, 455 - 458.
20. L. Bernardi, B. F. Bonini, E. Capitò, G. Dessole, M. Fochi, M. Comes-Franchini, A. Ricci, Synlett 2003, 1778 - 1782.
21. C. Agami, F. Couty, G. Evano, Org. Lett. 2000, 2, 2085 - 2088.
22. C. Schneider, C. Börner, Synlett 1998, 652 - 654.
23. F. Brackmann, A. de Meijere, Chem. Rev. 2007, 107, 4538 - 4583.
24. Selected references
25. J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584 - 1585
26. G.-D. Tebben, K. Rauch, C. Stratmann, C. M. Williams, A. de Meijere, Org. Lett. 2003, 5, 483 - 485
27. N. Ouhamou, Y. Six, Org. Biomol. Chem. 2003, 1, 3007 - 3009
28. C. Madelaine, N. Ouhamou, A. Chiaroni, E. Vedrenne, L. Grimaud, Y. Six, Tetrahedron 2008, 64, 8878 - 8898
29. C. Madelaine, A. K. Buzas, J. Kowalska-Six, Y. Six, B. Crousse, Tetrahedron Lett. 2009, 50, 5367 - 5371.
30. -3. CCDC-777553 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
31. K. Mai, G. Patil, Tetrahedron Lett. 1984, 25, 4583 - 4586.
32. -3. CCDC-777551 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
33. Y. Gao, F. Sato, J. Org. Chem. 1995, 60, 8136 - 8137.
34. -3. CCDC-777552 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
35. 2, see:, J. E. Baldwin, D. R. Spring, R. C. Whitehead, Tetrahedron Lett. 1998, 39, 5417 - 5420.
36. H. Brombacher, H. Vahrenkamp, Inorg. Chem. 2004, 43, 6054 - 6060
37. F. Orsini, Synthesis 1985, 500 - 503
38. N. Goasdoué, M. Gaudemar, J. Organomet. Chem. 1972, 39, 17 - 27.
39. For a discussion on the structure of metalated nitriles as a function of the metal, see:, F. F. Fleming, S. Gudipati, Eur. J. Org. Chem. 2008, 5365 - 5374.
40. Zincioiminiums
41. G. Bégis, D. E. Cladingboel, W. B. Motherwell, Chem. Commun. 2003, 2656 - 2657
42. G. Bégis, D. E. Cladingboel, W. B. Motherwell, T. D. Sheppard, D. A. Tocher, Synthesis 2005, 3186 - 3188
43. W. B. Motherwell, G. Bégis, D. E. Cladingboel, L. Jerome, T. D. Sheppard, Tetrahedron 2007, 63, 6462 - 6476
44. G. Bégis, D. E. Cladingboel, L. Jerome, W. B. Motherwell, T. D. Sheppard, Eur. J. Org. Chem. 2009, 1532 - 1538
45. L. Jerome, T. D. Sheppard, A. E. Aliev, W. B. Motherwell, Tetrahedron Lett. 2009, 50, 3709 - 3712
46. A. Serieys, C. Botuha, F. Chemla, F. Ferreira, A. Pérez-Luna, Tetrahedron Lett. 2008, 49, 5322 - 5323.
47. Lithioiminiums:, M. Buswell, I. Fleming, U. Ghosh, S. Mack, M. Russell, B. P. Clark, Org. Biomol. Chem. 2004, 2, 3006 - 3017.
48. For selected reviews on related α-azametalo-carbenoids, see
49. L. S. Hegedus, Tetrahedron 1997, 53, 4105 - 4128
50. T. S. Powers, W. D. Wulff, J. Quinn, Y. Shi, W. Q. Jiang, R. P. Hsung, M, Parisi, A Rahm, X. W. Jiang, G. A. Yap, A. L. Rheingold, J. Organomet. Chem. 2001, 617, 182 - 208.
51. Selected references
52. C. P. Casey, A. J. Shusterman, N. W. Vollendorf, K. J. Haller, J. Am. Chem. Soc. 1982, 104, 2417 - 2423
53. C. P. Casey, N. W. Vollendorf, K. J. Haller, J. Am. Chem. Soc. 1984, 106, 3754 - 3764
54. M. J. McGeary, T. L. Tonker, J. L. Templeton, Organometallics 1985, 4, 2102 - 2106
55. M. Brookhart, W. B. Studabaker, Chem. Rev. 1987, 87, 411 - 432
56. A. Ogawa, N. Takami, M. Sekiguchi, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1992, 114, 8729 - 8730
57. S. Couty, C. Meyer, J. Cossy, Synlett 2007, 2819
58. Z. F. Al-Rashid, R. P. Hsung, Org. Lett. 2008, 10, 661 - 663.
59. Selected references
60. U. Schöllkopf, M. Hauptreif, J. Dippel, M. Nieger, E. Egert, Angew. Chem. 1986, 98, 187 - 189
61. Angew. Chem. Int. Ed. Engl. 1986, 25, 192 - 193
62. A. Ogawa, N. Takami, T. Nanke, S. Ohya, T. Hirao, Tetrahedron 1997, 53, 12895 - 12902
63. I. Merino, L. S. Hegedus, Organometallics 1995, 14, 2522 - 2531
64. J. Barluenga, F. Aznar, I. Gutiérrez, S. García-Granda, M. A. Llorca-Baragaño, Org. Lett. 2002, 4, 4273 - 4276
65. R. P. Wurz, A. B. Charrette, J. Org. Chem. 2004, 69, 1262 - 1269.
66. For the first 2-azonia-Cope rearrangement, see:, R. M. Horowitz, T. A. Geissman, J. Am. Chem. Soc. 1950, 72, 1518.
67. For selected recent examples, see
68. M. Rueping, A. Antonchick, Angew. Chem. Int. Ed. 2008, 47, 10090 - 10093
69. M. Sugiura, C. Mori, S. Kobayashi, J. Am. Chem. Soc. 2006, 128, 11038 - 11039
70. S. Stas, K. A. Tehrani, G. Laus, Tetrahedron 2008, 64, 3457 - 3463
71. B. F. Johnson, E. L. Marrero, W. A. Turley, H. A. Lindsay, Synlett 2007, 893 - 896.
72. For reviews of the aza-Cope-Mannich rearrangement cyclization and related reactions, see
73. L. E. Overman, Aldrichimica Acta 1995, 28, 107 - 120
74. L. Overman, Acc. Chem. Res. 1992, 25, 352 - 359
75. L. Overman, D. Ricca, in Comprehensive Organic Synthesis Vol. 8 (Ed.:, B. M. Trost,), Pergamon, New York, 1991, pp. 1007 - 1046
76. J. Royer, M. Bonin, L. Micouin, Chem. Rev. 2004, 104, 2311 - 2352.
77. For an example of isomerization of a carbene to a nonstabilized azomethine ylide, see:, X. Cattoën, S. Solé, C. Pradel, H. Gornitzka, K. Miqueu, D. Bourrissou, G. Bertrand, J. Org. Chem. 2003, 68, 911 - 914.
78. Pyrrolidine ring formation by inter- and intramolecular [3+2] cycloadditions between (2-azaallyl)lithium and nonactivated alkenes is well-documented; for selected reviews, see
79. W. H. Pearson, Pure Appl. Chem. 2002, 74, 1339 - 1347
80. W. H. Pearson, P. Stoy, Synlett 2003, 0903 - 0921.
81. Select reviews
82. L. M. Harwood, R. J. Vickers, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Eds.:, A. Padwa, W. H. Pearson,), Wiley, New York, 2003, Chapter 3, p. 169
83. C. Najera, J. M. Sansano, Curr. Org. Chem. 2003, 7, 1105 - 1150
84. I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765 - 2809.
85. For selected references on azomethine ylide formation from (2-azoniaallyl)stannanes or (2-azoniaallyl)silanes, see
86. M. T. Epperson, D. Y. Gin, Angew. Chem. 2002, 114, 1856 - 1858
87. Angew. Chem. Int. Ed. 2002, 41, 1778 - 1780
88. W. H. Pearson, P. Stoy, Y. Mi, J. Org. Chem. 2004, 69, 1919 - 1939
89. G. Bélanger, V. Darsigny, M. Doré, F. Lévesque, Org. Lett. 2010, 12, 1396 - 1399, and references therein.
90. For a recent example of a 6-endo cyclization of an iminium onto an alkene of an organometallic species, see:, C. Kim, H. J. Bae, J. H. Lee, W. Jeong, H. Kim, V. Sampath, Y. H. Rhee, J. Am. Chem. Soc. 2009, 131, 14660 - 14661.
91. Ring contraction of lithio N-Boc-4-chloropiperidine to 2-azabicylo[3.1.0]hexane has precedent, see
92. P. Beak, S. Wu, E. K. Yum, Y. M. Jun, J. Org. Chem. 1994, 59, 276 - 277
93. Y. S. Park, P. Beak, Tetrahedron 1996, 52, 12333 - 12350.
94. C-C single bond rotation in acyclic N-homoallyl iminium ions was shown to be even faster than intramolecular Mannich cyclization between two oriented reactive donor and acceptor, see:, E. J. Jacobsen, J. Levin, L. E. Overman, J. Am. Chem. Soc. 1988, 110, 4329 - 4336.
95. R. J. Doedens, G. P. Meier, L. E. Overman, J. Org. Chem. 1988, 53, 685 - 690
96. H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Synthesis, Vol. 4 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991, pp. 1047 - 1082.
97. M. Lukowski, K. Jacobs, P. Hsueh, H. A. Lindsay, M. C. Milletti, Tetrahedron 2009, 65, 10311 - 10316.
98. R. P. Polniaszek, S. E. Belmont, R. Alvarez, J. Org. Chem. 1990, 55, 215 - 223.
99. For a general review on the use of α-phenylethylamine as a chiral reagent in the stereodifferentiation of prochiral substrates, see:, E. Juaristi, J. L. León-Romo, A. Reyes, J. Escalante, Tetrahedron: Asymmetry 1999, 10, 2441 - 2495.
100. The sense of asymmetric induction is the sense generally observed for 1,3-stereoinduction for chiral imines derived from phenylethylamine, see reference [45].
101. R. J. Linderman, T. V. Anklekar, J. Org. Chem. 1992, 57, 5078 - 5080
102. R. J. Linderman, K. Chen, J. Org. Chem. 1996, 61, 2441 - 2453
103. J. Cossrow, S. D. Rychnovsky, Org. Lett. 2002, 4, 147 - 150
104. S. D. Rychnovsky, J. Cossrow, Org. Lett. 2003, 5, 2367 - 2370.
105. Moreover this stereochemical outcome is also consistent with that of intramolecular cyclizations of vinylsilanes onto α-cyanoenamines leading to 2,6-disubstituted piperidines, see
106. P. Castro, L. E. Overman, X. Zhang, P. S. Mariano, Tetrahedron Lett. 1993, 34, 5243 - 5246
107. T.-K. Yang, T.-F. Teng, J.-H. Lin, Y.-Y. Lay, Tetrahedron Lett. 1994, 35, 3581 - 3582.
108. For a discussion on the conformational requirements for cyclopropane formation by internal nucleophilic substitution, see
109. D. Beruben, I. Marek, J. F. Normant, N. Platzer, J. Org. Chem. 1995, 60, 2488 - 2501
110. F. Ferreira, C. Herse, E. Riguet, J. F. Normant, Tetrahedron Lett. 2000, 41, 1733 - 1736.
111. In contrast, (2-azaallyl)zinc intermediates have a precedent, see:, V. Lyaskovskyy, R. Frölich, E.-U. Würthwein, Chem. Eur. J. 2007, 13, 3113 - 3119.
112. For other selected examples of 2-aza-Cope rearrangements with no epimerization, see
113. P. G. M. Wuts, Y. W. Jung, J. Org. Chem. 1988, 53, 1957 - 1965
114. H.-S. Cheng, A.-H. Seow, T.-P. Loh, Org. Lett. 2008, 10, 2805 - 2807, and reference [33b].