Asymmetric protonations of enol derivatives

Synlett

Volumn , Issue SPEC. ISS., 1997, Pages 411-420

  Yanagisawa, Akira ^a   Ishihara, Kazuaki ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002284321     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-6131     Document Type: Article

References (108)

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54. 3).
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61. Studies on the catalytic enantioselective protonation of enolates: (a) Fehr, C.; Stempf, I.; Galindo, J. Angew. Chem. Int. Ed. Engl. 1993, 32, 1044.
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66. Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Kuribayashi, T.; Yamamoto, H. unpublished results.
67. A study of protonolysis of silyl enol ethers carried out by Novice et al. indicated C-protonation in the case of tert-butyl dimethylsilyl enol ethers while no conclusion was arrived at for trimethyl silyl enol ethers. Novice, M. H.; Seikaly, H. R.; Seiz, A. D.; Tidwell, T. T. J. Am. Chem. Soc. 1980, 102, 5835.
68. As other studies relative to our present interest in LBA, we recently described the application of Brønsted acid assisted chiral Lewis acid (BLA) to the catalytic enantioselective Diels-Alder reaction of α-substituted-α,β-enals and the asymmetric aza Diels-Alder and aldol-type reactions of imines. (a) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561.
69. (b) Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
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71. Ishihara, K.; Kaneeda, M; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 11179.
72. For references on regioselective preparation of thermodynamic silyl enol ethers, see: (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: San Diego, 1988; p 100.
73. (b) Krafft, M. E.; Holton, R. A. Tetrahedron Lett. 1983, 24, 1345.
74. Values are corrected for the regioisomeric purities of silyl enol ethers.
75. The increase in enantioselectivity for the protonation of 19 with (R)-18, as compared to that in our original paper (97 vs. 79% ee) results from using 19 which was purified by redistillation.
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82. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 1985, 26, 5037.
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84. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett 1991, 807. Diastereoselective halogenation of chiral imide enolates:
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86. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Amer. Chem. Soc. 1990, 112, 4011. Diastereoselective halogenation of chiral sultams:
87. (f) W. Oppolzer, Pure. Appl. Chem. 1990, 62, 1241. Diastereoselective halogenation of chiral dioxanones:
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89. (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992)6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids:
90. (i) M Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 1992, 33, 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate:
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92. 3: (a) J. Kenyon, G. Lipscomb, and H. Phillips, J. Chem. Soc. 1931, 2275.
93. 2 and hydrochloric acid:
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98. N2 reaction of α-sulfonyloxialkanoate with potassium fluoride:
99. (h) E. Fritz-Langhals and G. Schütz, Tetrahedron Lett. 1993, 34, 293.
100. Diastereoselective halogenation of chiral acetals, see: (a) C. Giordano, G. Castaldi, S. Cavicchioli, and M. Villa, Tetrahedron 1989, 45, 4243.
101. (b) C. Giordano, L. Coppi, and A. Restelli, J. Org. Chem. 1990, 55, 5400 and references cited therein.
102. It was ascertained that the present protonation of 19 using 18 did not occur via tin enoltae by the follow control experiment: 19 was stable in the presence of tin tetrachloride (1 equiv) at -78°C over 2.5 h. Kuwajima et al. reported the formation of α-trichlorostannyl ketones in the reaction of tin tetrachloride with silyl enol ethers at 35°C. Nakamura, E.; Kuwajima, I. Chem. Lett. 1983, 59.
103. Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854.
104. The same reaction-conditions with entry 2 in Table 8 were used.
105. Values in parentheses were corrected for the regioisomeric purities of silyl enol ethers.
106. The same reaction-conditions with entry 2 in Table 8 were used except that tin tetrachloride was reduced to 50 mol%.
107. The same reaction-conditions with entry 2 in Table 9 were used.
108. The disilyl ether of (R)-BINOL was not observed at all. In fact, the mixture of tin tetrachloride and the monosilyl ether of (R)-BINOL was less reactive for 19 (-78°C, 5 min: <21% conversion). Considering the steric and electronic effects of the trimethylsilyl group, the rigid formation of LBA from (R)-BINOL and tin tetrachloride should be rather difficult.