Enantioselective C-C bond formation to sulfonylimines through use of the 2-pyridinesulfonyl group as a novel stereocontroller

Chemistry - A European Journal

Volumn 14, Issue 7, 2008, Pages 2145-2152

  Nakamura, Shuichi ^a   Nakashima, Hiroki ^a   Sugimoto, Hideki ^a   Sano, Hideaki ^a   Hattori, Masataka ^a   Shibata, Norio ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Grignard reactions; Mannich type reactions; Stereocontroller; Strecker type reaction

Indexed keywords

ACIDS; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; OXYGEN; PYRIDINE; STEREOCHEMISTRY; SULFUR;

ASYMMETRIC SYNTHESIS; GRIGNARD REACTIONS; MANNICH-TYPE REACTIONS; STEREOCONTROLLER; STRECKER-TYPE REACTION;

COORDINATION REACTIONS;

CARBON; IMINE; PYRIDINE DERIVATIVE; SULFONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CARBON; IMINES; MOLECULAR STRUCTURE; PYRIDINES; STEREOISOMERISM; SULFONES;

EID: 48249106576     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701425     Document Type: Article

References (112)

1. For reviews, see: a) A. Jahansson, Contemp. Org. Synth. 1995, 2, 393-407;
2. b) E. Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946, and references therein;
3. c) G. Alvaro, D. Savoia, Synlett 2002, 651-673;
4. d) R. Bloch, Chem. Rev. 1998, 98, 1407-1438.
5. For reviews covering chiral Lewis acids, see: a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094;
6. b) T. Vilaivan, W. Bhanthumnavin, Y. Sritana-Anam, Curr. Org. Chem. 2005, 9, 1315-1392;
7. c) G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541-2569;
8. d) D. Ferraris, Tetrahedron 2007, 63, 9581-9597.
9. For recent reviews covering chiral organocatalysts, see: a) A. Berkessel, H. Grùger, Asymmetric Organocatalysis. Wiley-VCH, Weinheim, 2005, Chapter 5.2, pp. 97-108;
10. b) T. Fujie, C. F. Barbas, III, Enantioselective Organocatalysis (Ed.: P. I. Dalko), Wiley-VCH, Weinheim, 2007, Chapter 2.1, pp. 38-51.
11. For reviews of the enantioselective reactions of acylhydrazones, see: a) S. Kobayashi, M. Sugiura, C. Ogawa, Adv. Synth. Catal. 2004, 346, 1023-1034;
12. b) G. K. Friestad, Eur. J. Org. Chem. 2005, 3157-3172;
13. for the reactions of N-(2-hydroxyphenyl)imines. see: c) H. Ishitani, S. Kobayashi. Tetrahedron Lett. 1996, 37, 7357-7360;
14. d) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153-7154;
15. e) S. Kobayashi, S. Komiyama, K. Ishitani, Angew. Chem. 1998, 110, 1026-1028;
16. Angew. Chem. Int. Ed. 1998, 37, 979-981;
17. f) T. Gastner, H. Ishitani, R. Akiyama, S. Kobayashi. Angew. Chem. 2001, 113, 1949-1951;
18. Angew. Chem. Int. Ed. 2001, 40, 1896-1898.
19. a) J. Kovacs, U. R. Ghalak, J. Org. Chem. 1966, 31, 119-121;
20. b) S. Ji, L. B. Gortler, A. Waring, A. Battisti, S. Bank, W. D. Closson, P. Wriede, J Am. Chem. Soc. 1967, 89, 5311-5312. Conversion of N-sulfonamides into N-alkyl-N-sulfonyl compounds or N-Boc-N-sulfonyl compounds prior to the cleavage is needed for removal of a losyl group from primary amines,
21. see: c) B. Nyasse, L. Grehn, U. Ragnarsson, Chem. Commun. 1997, 1017-1018, and references therein,
22. d) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3083-3085;
23. Angew. Chem. Int. Ed. 2001, 40, 2995-2997.
24. a) H. Sugimoto, S. Nakamura, Y. Watanabe, T. Toru, Tetrahedron: Asymmetry 2003, 14, 3043-3045;
25. b) H. Sugimoto. K. Kobayashi, S. Nakamura, T. Toru, Tetrahedron Lett. 2004, 45, 4213-4216:
26. c) Y. Watanabe, N. Mase, R. Furue, T. Toru, Tetrahedron Lett. 2001, 42, 2981 -2984.
27. For a recent review on chiral relay effects, see: a) O. Corminboeuf, L. Quaranta, P. Renaud, M. Liu, C. P. Jasperse, M. P. Sibi, Chem. Eur. J. 2003, 9, 28-35;
28. for a recent contribution, see: b) M. P. Sibi. L. M. Stanley, X. Nie, L. Venkatraman, M. Liu, C, P. Jasperse, J. Am. Chem. Soc. 2007, 129, 395-405.
29. a) P. Mauleón, J. C. Carretero, Chem. Commun. 2005, 4961-4963;
30. b) J. Esquivias, R. G. Arrayás, J. C. Carretero, J. Org. Chem. 2005, 70, 7451-7454.
31. T. Llamas, R. G. Arrayás, J. C. Carretero, Angew. Chem. 2007, 119, 3393-3396;
32. Angew. Chem. Int. Ed. 2007, 46, 3329-3332.
33. T. Llamas, R. G. Arrayás, J. C. Carretero, Org. Lett. 2006, 8, 1795-1798.
34. J. Esquivias, R. G. Arrayás, J. C Carretero, J. Am. Chem. Soc. 2007, 129, 1480-1481.
35. A. S. González, R. G. Arrayás, J. C. Carretero, Org. Lett. 2006, 8, 2977-2980.
36. H. Morimoto, G. Lu, N. Aoyama, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 9588-9589.
37. For preliminary reports, see: a) S. Nakamura, N. Sato, M. Sugimoto, T. Toru, Tetrahedron: Asymmetry 2004, 15, 1513-1516;
38. b) H. Sugimoto, S. Nakamura, M. Hattori, S. Ozeki, N. Shibata, T. Toru, Tetrahedron Lett. 2005, 46, 8941-8944;
39. c) S. Nakamura, H. Nakashima, H. Sugimoto, N. Shibata, T. Toru, Tetrahedron Lett. 2006, 47, 7599-7602;
40. d) S. Nakamura, H. Sano, H. Nakashima, K. Kubo, N. Shibata, T. Toru, Tetrahedron Lett., 2007, 48, 5565-5568.
41. For a review, see: S. Bräse, T. Baumann, S. Dahmen, H. Voget, Chem. Commun. 2007, 1881-1890.
42. 3, see: S. Saito, K. Hatanaka, H. Yamamoto, Synlett 2001, 1859-1861.
43. Treatment of la with a catalytic amount (0.3 equiv) of bis(oxazoline) A and MeMgBr gave 2a with 29% ee.
44. There are some examples of enantioselective reactions of nitrones with Grignard reagents: a) Y. Ukaji, T. Hatanaka, A. Ahmed, K. Inomata, Chem. Lett. 1993, 1313-1316;
45. b) F. L. Merchan, P. Merino, I. Rojo, T. Tejero, A. Dondoni, Tetrahedron: Asymmetry 1996, 7, 667-670.
46. For reviews, see: a) L. Yet, Angew. Chem. 2001, 113, 900-902;
47. Angew. Chem. Int. Ed. 2001, 40, 875-877;
48. b) H. Gröger, Chem. Rev. 2003, 103, 2795-2827. For a recent report on catalytic enantioselective Strecker-type reactions in the presence of chiral Lewis acids, see:
49. c) S. Masumoto, H. Usuda, M. Suzuki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 5634-5635;
50. d) J. Blacker, L. A. Clutterbuck, M. R. Crampton, C. Grosjean, M. North, Tetrahedron: Asymmetry 2006, 17, 1449-1456.
51. For recent reports on catalytic enantioselective Strecker-type reactions in the presence of chiral organocatalysts, see: e) X. Huang, J. Huang, Y. Wen, X. Feng, Adv. Synth. Catal. 2006, 348, 2579-2584;
52. f) R. P. Herrera, V. Sgarzani, L. Bernardi, F. Fini, D. Perrersen, A. Ricci, J. Org. Chem. 2006, 71, 9869-9872;
53. g) J. Huang, X. Liu, Y. Wen, B. Qin, X. Feng, J. Org. Chem. 2007, 72, 204-208;
54. h) M. Rueping, E. Sugiono, S. A. Moreth, Adv. Synth. Catal. 2007, 349, 759-764;
55. i) S. C. Pan, B. List, Org. Lett. 2007, 9, 1149-1151;
56. j) S. C. Pan, P. J. Zhou, B. List, Angew. Chem. 2007, 119, 618-620;
57. Angew. Chem. Int. Ed. 2007, 46, 612-614.
58. Catalytic enantioselective Strecker-type reactions of N-(trimelhyl-phenylsulfonyl)imines derived from aliphatic aldehydes by use of chiral quaternary ammonium salts afford the products with high ees, although this catalytic system cannot be applied to the reactions of aromatic aldimines, see: a) T. Ooi, Y. Uematsu, K. Maruoka, J. Am. Chem. Soc. 2006, 128, 2548-2549;
59. b) T. Ooi, Y. Uematsu, J. Fujimolo, K. Fukumoto, K. Maruoka, Tetrahedron Lett. 2007, 48, 1337-1340.
60. For achiral Strecker-type reactions with N-tosylimines, see: a) B. A. B. Prasad, A. Bisai, V. K. Singh, Tetrahedron Lett. 2004, 45, 9565-9567;
61. b) E. Takahashi, H. Fujisawa, T. Yanai, T. Mukaiyama, Chem. Lett. 2005, 34, 318-319.
62. 3SnCN, TMSCN, TBDPSCN, and KCN as a cyanation reagent, obtaining the product 3a in low yield.
63. 3/H. and chiral salen/AlCl complexes afforded the product 3a either in low yields or with low enantioselectivities.
64. Similar observations of the reversal of stereochemistry have been reported, see: a) M. P. Sibi, J. Ji, J. Org. Chem. 1997, 62, 3800-3801;
65. b) M. P. Sibi, H. Matsunaga, Tetrahedron Lett. 2004, 45, 5925-5929.
66. 2 and DBFOX reaction did not afford the product 3a.
67. 2/ligand F catalyst can be used most efficiently for the reactions of 1a, but the Stecker-type reactions with other sulfonylimines 1i-n and this catalyst afford the product in low yield and with low enantioselectivity.
68. Enantioselective Synthesis of β-Amino Acids (Eds.; E. Juaristi, V. A. Soloshonok), Wiley-VCH, New York, 2005.
69. E. F. Kleinmann, in Comprehensive Organic Synthesis, Vol.2 (Eds.; B. M. Trost, I. Fleming), Pergamon Press, New York, 1991. Chapter 4.1.
70. a) T. Hintermann. D. Seebach, Chimia 1997, 50, 244-247;
71. b) D. Seebach, J. L. Matthews, Chem. Commun. 1997, 2015-2022;
72. c) U. Koert, Angew. Chem. 1997, 109, 1922-1923;
73. Angew. Chem. Int. Ed. Engl. 1997, 36, 1836-1837;
74. d) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180.
75. For reviews on the asymmetric Mannich reaction, see: a) A. Córdova, Acc. Chem. Res. 2004, 37, 102-112;
76. b) M. Ueno, S. Kobayashi, in Enantioselective Synthesis of β-Amino Acids (Eds.: E. Juaristi, V. A. Soloshonok), Wiley-VCH, New York, 2005, Chapter 6.
77. For recent reports on the catalytic asymmetric Mannich reaction in the synthesis of β-amino acid derivatives, see: a) N. S. Josephsohn, E. L. Carswell, M. L. Snapper, A. H. Hoveyda, Org. Lett. 2005, 7, 2711-2713;
78. b) M. Sugiura, S. Kobayashi, Angew. Chem. 2005, 117, 5306-5317;
79. Angew. Chem. Int. Ed. 2005, 44, 5176-5186;
80. c) S. Kobayashi, K. Arai, H. Shimizu, Y. Ihori, H. Ishitani, Y. Yamashita, Angew. Chem. 2005, 117, 771-774;
81. Angew. Chem. Int. Ed. 2005, 44, 761-764;
82. reaction with β-ketoesters, see: d) S. Lou, B. M. Taoka, A. Ting, S. E. Schaus, J. Am. Chem. Soc. 2005, 127, 11256-11257;
83. e) Y. Hamashima, N. Sasamoto, D. Hotta, H. Somei, N. Umebayashi, M. Sodeoka, Angew. Chem. 2005, 117, 1549-1553;
84. Angew. Chem. Int. Ed. 2005, 44, 1525-1529;
85. for recent reports covering organocatalysts; f) J. Song, Y. Wang, L. Deng, J. Am. Chem. Soc. 2006, 128, 6048-6049;
86. g) F. Fini, L. Bernardi, R. P. Herrera, D. Pettersen, A. Ricci, V. Sgarzani, Adv. Synth. Catal. 2006, 348, 2043-2046;
87. h) J. Song, H. Shih, L. Deng, Org. Lett. 2007, 9, 603-607;
88. i) Y. Suto, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 500-501;
89. j) A. Sigh, R. A. Yoder, B. Shen, J. N. Johnston, J. Am. Chem. Soc. 2007, 129, 3466-3467;
90. k) M. Yamanaka, J. Itoh, K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2007, 129, 6756-6764.
91. For enantioselective Mannich-type reactions of highly electronically activated α-tosylimino esters, see: a) A. E. Taggi, A. M. Hafez, T. Lectka. Acc. Chem. Res. 2003, 36, 10-19;
92. b) D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548-4549;
93. c) D. Ferraris, B. Young, C. Cox, T. Dudding, W. J. Drury, III, L. Ryzhkov, A. E. Taggi, T. Lectka, J. Am. Chem. Soc. 2002, 124, 67-77;
94. d) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359-2367;
95. for enantioselective reactions of simple α-sulfonylimines, see: e) L. Bernardi, A. S. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2003, 68, 2583-2591;
96. f) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439-4442;
97. Angew. Chem. Int. Ed. 2005, 44, 4365-4368, see also ref. [5 d].
98. High enantioselectivity was not shown in reactions in other solvents or with various other copper(II) salts.
99. a) C. Goulaouic-Dubois, A. Guggisberg, M. Hesse, J. Org. Chem. 1995, 60, 5969-5972;
100. b) C. S. Pak, D. S. Lim, Synth. Commun. 2001, 31, 2209-2214.
101. II complex has been proposed, see:
102. a) E. J. Corey, K. Ishihara, Tetrahedron Lett. 1992, 33, 6807-6810;
103. b) M. P. Sibi, J. B. Sausker, J. Am. Chem. Soc. 2002, 124, 984-991. The octahedral structure has been also proposed:
104. c) M. P. Sibi, G. Petrovic, J. Zimmerman, J. Am. Chem. Soc. 2005, 127, 2390-2391;
105. d) K. V. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 1998, 63, 5483-5488.
106. Another plausible reaction mechanism through a seven-membered transition state in which the pyridine nitrogen is coordinated to magnesium may be considered, but it is ruled out because the transition state would form the R isomer preferentially.
107. Spartan '06 PM3, Y. Shao, L. F. Molnar, Y. Jung, J. Kussmann, C. Ochsenfeld, S. T. Brown, A. T. B. Gilbert, L. V. Slipchenko, S. V. Levchenko, D. P. O'Neill, R. A. DiStasio, Jr., R. C. Lochan, T. Wang, G. J. O. Beran, N. A. Besley, J. M. Herbert, C. Y. Lin, T. Van Voorhis, S. H. Chien, A. Sodt, R. P. Steele, V. A. Rassolov, P. E. Maslen, P. P. Korambath, R. D. Adamson, B. Austin, J. Baker, E. F. C. Byrd, H. Dachsel, R. J. Doerksen, A. Dreuw, B. D. Dunietz, A. D. Dutoi, T. R. Furlani, S. R. Gwaltney, A. Heyden, S. Hirata, C.-P. Hsu, G. Kedziora, R. Z. Khalliulin, P. Klunzinger, A. M. Lee, M. S. Lee, W. Liang, I. Lotan, N. Nair, B. Peters, E. 1. Proynov, P. A. Pieniazek, Y. M. Rhee. J. Ritchie, E. Rosta, C. D. Sherrill, A. C. Simmonett, J. E. Subotnik, H. L. Woodcock, III, W. Zhang, A. T. Bell, A. K. Chakraborty, D. M. Chipman, F. J. Keil, A. Warshel, W. J. Hehre, H. F. Schaefer, III, J. Kong, A. I. Krylov, P. M. W. Gill, M. Head-Gordon, Phys. Chem. Chem. Phys. 2006, 8, 3172-3191.
108. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, O. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004. [39] All optimized structures were confirmed to have no negative frequency by frequency calculations. All transition structures were found to have only one negative eigenvalue with the corresponding eigenvector involving the formation of newly created C-C bonds. The transition states reported were shown to belong to the studied reaction through the intrinsic reaction coordinate (IRC).
109. II complex did not result in convergence.
110. M.-V. Rangaishenvi, B. Singaram, H.-C. Brown, J. Org. Chem. 1991, 56, 3286-3294.
111. H. Kunz, D. Schanzenbach, Angew. Chem. 1989, 101, 1063-1065;
112. Angew. Chem. Int. Ed. Engl. 1989, 28, 1042-1043.