Intramolecular sulfur transfer in N-enoyl oxazolidine-2-thiones promoted by Brønsted acids. Practical asymmetric synthesis of β-mercapto carboxylic acids and mechanistic insights

Journal of the American Chemical Society

Volumn 128, Issue 47, 2006, Pages 15236-15247

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   López, Rosa ^a   González, Pedro B ^a   Gómez Bengoa, Enrique ^a   Saá, José M ^a,b   Linden, Anthony ^a,c  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

^c UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CARBOXYLIC ACIDS; COMPLEXATION; ESTERS; OLEFINS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

LEWIS ACIDS; PROMOTED REACTIONS; SULFUR TRANSFER PROCESS; THIONES;

SULFUR COMPOUNDS;

ACETIC ACID; ACID; ALKENE DERIVATIVE; BRONSTED ACID; CARBOXYLIC ACID DERIVATIVE; DIFLUOROACETIC ACID; ESTER DERIVATIVE; LEWIS ACID; METHANOL; OXAZOLIDINE DERIVATIVE; PROTON; SODIUM BOROHYDRIDE; SULFUR; THIOL DERIVATIVE; TRIFLUOROACETIC ACID; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL REACTION; CORRELATION ANALYSIS; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 33845195665     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0654027     Document Type: Article

References (109)

1. For reviews on the synthesis of thiols, sulfides, and derivatives, see: (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2001, 335-354 and previous articles in the series.
2. For a review on C-S bond construction, see: (b) Kondo, J.; Mitsudo, T. Chem. Rev. 2000, 100, 3205-3220.
3. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
4. Reviews: (a) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Angew. Chem., Int. Ed. 2000, 39, 2980-3010.
5. (b) Rovner, S. L. Chem. Eng. News 2004, 82(42), 46.
6. For leading references, see: (a) Wu, M.-J.; Wu, C.-C.; Tseng, T.-C. J. Org. Chem. 1994, 59, 7188-7189.
7. (b) Tsai, W.-J.; Lin, Y.-T.; Uang, B.-J. Tetrahedron: Asymmetry 1994, 5, 1195-1198.
8. (c) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190.
9. (d) Taber, D. F.; Gorski, G. J.; Liable-Sands, L. M.; Rheingold, A. L. Tetrahedron Lett. 1997, 38, 6317-6318.
10. (e) Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron 1997, 53, 2421-2438 and references therein.
11. (f) Lin, C-H.; Yang, K.-S.; Pan, J.-P.; Chen, K. Tetrahedron Lett. 2000, 41, 6815-6819.
12. (a) Michieletto, I.; Fabris, F.; De Lucchi, O. Tetrahedron: Asymmetry 2000, 11, 2835-2841.
13. (b) Node, M.; Nishide, K.; Shigeta, Y.; Shiraki, H.; Obata, K. J. Am. Chem. Soc. 2000, 122, 1927-1936.
14. (c) Nishide, K.; Ohsugi, S.-i.; Shiraki, H.; Tamakita, H.; Node, M. Org. Lett. 2001, 3, 3121-3124.
15. (d) Nishide, K.; Ozeki, M.; Kunisgige, H.; Shigeta, Y.; Patra, P. K.; Hagimoto, Y.; Node, M. Angew. Chem., Int. Ed. 2003, 42, 4515-4517.
16. (e) Ozeki, M.; Nishide, K.; Teraoka, F.; Node, M. Tetrahedron: Asymmetry 2004, 15, 895-907.
17. (f) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Gonzalez, L. Eur. J. Org. Chem. 2004, 1492-1499.
18. Reviews on enantioselective conjugate additions: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061.
19. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196.
20. (c) Jha, S. C.; Joshi, N. N. Arkivoc 2002, 7, 167-196.
21. (a) Colonna, S.; Re, A.; Wynberg, H. J. Chem. Soc., Perkin Trans. 1 1981, 547-552.
22. (b) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363-366.
23. (c) Nishimura, K.; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975.
24. (d) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044.
25. (e) Emori, E.; Iida, T.; Shibasaki, M. J. Org. Chem. 1999, 64, 5318-5320.
26. (f) Tomioka, K.; Okuda, M.; Nishimura, K.; Manaba, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144.
27. (g) Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675-8676.
28. (h) Saito, M.; Nakajima, M.; Hashimoto, S. Tetrahedron 2000, 56, 9589-9594.
29. (i) Saito, M.; Nakajima, M.; Hashimoto, S. Chem. Commun. 2000, 1851-1852.
30. (j) Kobayashi, S.; Ogawa, C.; Kawamura, M.; Sugiura, M. Synlett 2001, 983-985.
31. (k) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434.
32. (l) Prabagaran, N.; Sundararajan, G. Tetrahedron: Asymmetry 2002, 13, 1053-1058.
33. (m) Matsumoto, K.; Watanabe, A.; Uchida, T.; Ogi, K.; Katsuki, T. Tetrahedron Lett. 2004, 45, 2385-2388.
34. (n) Sauerland, S. J. K.; Kiljuren, E.; Koskinen, A. M. P. Tetrahedron Lett. 2006, 47, 1291-1293.
35. For earlier work, see: (a) Pracejus, H.; Wilcke, F.-W.; Hanemann, K. J. Prakt. Chem. 1977, 319, 219-229.
36. (b) Helder, R.; Arens, R.; Bolt, W.; Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 2181-2182.
37. (c) Kobayashi, N.; Iwai, K. J. Am. Chem. Soc. 1978, 100, 7071-7072.
38. (d) Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 363-366.
39. (e) Wynberg, H. Top. Stereochem. 1986, 16, 87-129.
40. (f) Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417-430.
41. (g) Suzuki, K.; Ikegawa, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1982, 55, 3277-3282.
42. For recent examples, see: (h) Ostendorf, M.; van der Neut, S.; Rutges, F. P. J. T.; Hiemstra, H. Eur. J. Org. Chem. 2000, 105-113.
43. (i) Toda, F.; Tanaka, K.; Sato, J. Tetrahedron: Asymmetry 1993, 4, 1771-1774.
44. (j) Ito, A.; Konishi, K.; Aida, T. Tetrahedron Lett. 1996, 37, 2585-2588.
45. (k) Skarzewski, J.; Zielinska-BLajet, M.; Turowska-Tyrk, I. Tetrahedron: Asymmetry 2001, 12, 1923-1928.
46. (l) Nishimura, K.; Tomioka, K. J. Org. Chem. 2002, 67, 431-434.
47. (m) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem., Int. Ed. 2002, 41, 338-340.
48. (n) Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710-15711.
49. (o) Li, B.-J.; Jiang, L.; Liu, M.; Chen, Y.-C.; Ding, L.-S.; Wu, Y. Synlett 2005, 603-606.
50. For methods giving rise to ee's regularly above 90%, see ref 8m,n.
51. (a) Palomo, C.; Oiarbide, M.; Dias, F.; Ortiz, A.; Linden, A. J. Am. Chem. Soc. 2001, 123, 5602-5603.
52. (b) Palomo, C.; Oiarbide, M.; Dias, F.; López, R.; Linden, A. Angew. Chem., Int. Ed. 2004, 43, 3307-3310.
53. See also: (a) Ortiz, A.; Quintero, L.; Hernández, H.; Maldonado, S.; Mendoza, G.; Bernés, S. Tetrahedron Lett. 2003, 44, 1129-1132.
54. (b) Ortiz, A.; Hernández, H.; Mendoza, G.; Quintero, L.; Bernès, S. Tetrahedron Lett. 2005, 46, 2243-2246.
55. For a chiral nonracemic thiol reagent that upon final sulphur interchange affords the formal conjugate addition of the SH group, see ref 5b-e.
56. 2O-promoted intramolecular cyclizations of N-propenoyl thioureas and N-propenoyl thiocarbamates leading to 1,3-thiazine derivatives, see: (a) Dzurilla, M.; Kutschy, P.; Kristian, P. Synthesis 1985, 933-934.
57. (b) Dzurilla, M.; Kutschy, P.; Koscik, D.; Toma, S. Collect. Czech. Chem. Commun. 1990, 55, 710-717.
58. (a) Kataoka, T.; Kinoshita, H.; Kinoshita, S.; Osamura, T.; Watanabe, S.-i.; Iwamura, T. Angew. Chem., Int. Ed. 2003, 42, 2889-2891.
59. (b) Kinoshita, H.; Takahashi, N.; Iwamura, T.; Watanabe, S.-i.; Kataoka, T.; Muraoka, O.; Tanabe, G. Tetrahedron Lett. 2005, 46, 7155-7158.
60. (c) Kinoshita, H.; Osamura, T.; Mizuno, K.; Kinoshita, S.; Iwamura, T.; Watanabe, S.-i.; Kataoka, T.; Muraoka, O.; Tanabe, G. Chem. - Eur. J. 2006, 12, 3896-3904.
61. Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. Chem. - Eur. J. 2004, 10, 484-493.
62. Brown, H. C.; Kanner, B. J. Am. Chem. Soc. 1966, 88, 986-992.
63. For reviews on substrate activation through hydrogen bonding, see: (a) Schreiner, P. R. Chem. Soc. Rev. 2003, 32, 289-296.
64. (b) Taylor, M. S.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2006, 45, 1520-1543.
65. For activation of carbonyl compounds by double hydrogen bonding, see: (c) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062-2064.
66. For protonated chiral catalysts, see: (d) Bolm, C.; Rantanen, T.; Schiffers, I.; Zani, L. Angew. Chem., Int. Ed. 2005, 44, 1758-1763.
67. For reviews on organocatalysis, see: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
68. (b) Benaglia, M.; Puglisi, A. Cozzi, F. Chem. Rev. 2003, 103, 3401-3430.
69. (c) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138-5175.
70. (d) Berkessel, A.; Gröger, H. Metal-Free Organic Catalysts in Asymmetric Synthesis; Wiley-VCH: Weinheim, 2004.
71. (e) Rouhi, A. M. Chem. Eng. News 2004, 82 (36), 41-45.
72. (f) Houk, K. N.; List, B. Acc. Chem. Res. 2004, 37, 487-631 (Special issue: Asymmetric Organocatalysis).
73. (g) Adv. Synth. Catal. 2004, 346, 1007-1249 (Special Issue: Organic Catalysis).
74. (h) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis. From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Wheinheim, 2005.
75. (i) Pihko, P. M. Lett. Org. Chem. 2005, 2, 398-403.
76. For an authoritative review on the concept of combined acid catalysis for asymmetric synthesis, see: Yamamoto, H.; Futatsugi, K. Angew. Chem., Int. Ed. 2005, 44, 1924-1942.
77. See ref 10 and the Supporting Information for details.
78. 5 has been described recently. See: Hernández, H.; Bernés, S.; Quintero, L.; Sansinenea, E.; Ortiz, A. Tetrahedron Lett. 2006, 47, 1153-1156.
79. 2O after 24 h.
80. For recent reviews on quaternary carbon stereocenters, see: (a) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
81. (b) Quaternary Stereocenters; Christoffers, J., Baro, A., Eds.; Wiley-VCH: 2005.
82. (c) Christoffers, J.; Baro, A. Adv. Synth. Catal. 2005, 347, 1473-1482.
83. α-Sulfenylation with moderate ee's: (a) Sobhani, S.; Fielenbach, D.; Marigo, M.; Wabnitz, T. C.; Jørgensen, K. A. Chem. Eur. J. 2005, 11, 5689-5694.
84. [2,3]-Sigmatropic rearrangement of sulfur ylide with double asymmetric induction: (b) Ma, M.; Peng, L.; Li, C.; Zhang, X. J. Am. Chem. Soc. 2005, 127, 15016-15017.
85. Alkylation of optically active α-lithiated sulfides: (c) Marr, F.; Fröhlich, R.; Hoppe, D. Org. Lett. 1999, 1, 2081-2083.
86. (d) Stratmann, O.; Kaiser, B.; Fröhlich, R.; Meyer, O.; Hoppe, D. Chem. - Eur. J. 2001, 7, 423-435.
87. (c) Marr, F.; Hoppe, D. Org. Lett. 2002, 4, 4217-4220.
88. α-Alkylation of thiolactone enolates: (f) Strijtveen, B.; Kellogg, R. M. Tetrahedron 1987, 43, 5039-5054.
89. (g) McFadden, J. M.; Frehywot, G. L.; Townsend, C. A. Org. Lett. 2002, 4, 3859-2862.
90. Mitsonobu type reaction of tertiary alcohols: (h) Ikegai, K.; Pluenpanupat, W.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2006, 79, 780-790.
91. Actually, during the preparation of the starting N-enoyl oxazolidine-2-thiones 2, variable degrees of E/Z isomerization were observed in the intermediate acids, esters, and/or acid chlorides, likely facilitated by the basic or acid reaction conditions employed.
92. See the SI for the corresponding plot of the NMR spectra.
93. Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. J. Am. Chem. Soc. 1991, 113, 1047-1049.
94. Prashad, M.; Har, D.; Kim, H.-Y.; Repic, O. Tetrahedron Lett. 1998, 39, 7067-7070.
95. For an efficient HPLC detection, adducts 16a-c as well as the corresponding racemic samples were derivatized to their dibenzoyl esters prior to analysis (for details, see Supporting Information).
96. (a) Lee, E.; Jeong, E. J.; Kang, E. J.; Sung, L. T.; Hong, S. K. J. Am. Chem. Soc. 2001, 123, 10131-10132.
97. (b) Reference 11a.
98. (31 ) Encyclopedia of Reagents for Organic Synthesis; Paquette, L. O., Ed.; John Wiley; Chichester. 1995; Vol. 1. p 530.
99. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
100. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
101. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
102. (c) Becke, A. D. Phys. Rev. A 1988, 38, 3098.
103. (d) Kohn, W.; Mecke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974.
104. Kock, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory; Wiley-VCH: Weinheim, 2001.
105. The calculated energy for 1a adopting a s-cis conformation instead was 5.3 kcal/mol higher. For a discussion on the energy preferences of different conformations of N-enoyl oxazolidinones, see: Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063-3064 and references therein.
106. For examples of carbonyl activation through hydrogen bonding that follows a DAD model, see: (a) Reference 17b.
107. (b) Reference 17c.
108. (c) Tonoi, T.; Mikami, K. Tetrahedron Lett. 2005, 46, 6355-6358.
109. For an example where a DDA activation model is proposed, see: (d) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336-1337.