Enantioselective Protonation of Ketene Bis(trimethylsilyl) Acetals Derived from α-Aryl-α-haloacetic Acids Using LBA

Croatica Chemica Acta

Volumn 69, Issue 2, 1996, Pages 513-517

  Ishihara, Kazuaki ^a   Nakamura, Shingo ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

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EID: 0001046786     PISSN: 00111643     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. 1 (97 vs. 79% ee) results from using 2 which was purified by redistillation.
2. (a) B. Koppenhoefer and V. Schurig, Org. Synth. Coll. Vol. VIII (1993) 434.
3. (b) B. Koppenhoefer, U. Trettin, and A. Wchtler, Synthesis (1994) 1141.
4. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
5. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
6. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
7. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
8. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
9. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
10. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
11. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
12. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
13. Stereoselective synthesis of α-halo carboxylic acid derivatives, see: Diastereoselective halogenation of chiral ketene silyl acetals: (a) W. Oppolzer and P. Dudfield, Tetrahedron Lett. 26 (1985) 5037. (b) W. Oppolzer, R. Pedrosa, and R. Moretti, Tetrahedron Lett. 27 (1986) 831. (c) L. Duhamel, P. Angibaud, J. R. Desmurs, and J. Y. Valnot, Synlett (1991) 807. Diastereoselective halogenation of chiral imide enolates: (d) D. A. Evans, J. A. Ellman, and R. L. Dorow, Tetrahedron Lett. 28 (1987) 1123. (e) D. A. Evans, T. C. Britton, J. A. Ellman, and R. L. Dorow, J. Am. Chem. Soc. 112 (1990) 4011. Diastereoselective halogenation of chiral sultams: (f) W. Oppolzer, Pure. Appl. Chem. 62 (1990) 1241. Diastereoselective halogenation of chiral dioxanones: (g) J. Zimmermann and D. Seebach, Helv. Chim. Acta 70 (1987) 1104. Enantioselective trapping of α-halogenated ketenes with (R)-pantolactone: (h) T. Durst and K. Koh, Tetrahedron Lett. 33 (1992) 6799. Enantioselective hydrogenation of α-fluoro-α-alkenoic acids: (i) M. Sabiri, L. Shao, T. Sakurai, and Y. Uchida, Tetrahedron Lett. 33 (1992) 7877. Enzyme-catalyzed kinetic resolution of ethyl α-fluorohexanoate: (j) P. Kalaritis and R. W. Regenye, Org. Synth. Coll. Vol. VIII (1993) 258.
14. 2 and hydrochloric acid: (c) S.-C. J. Fu, S. M. Birnbaum, and J. P. Greenstein, J. Am. Chem. Soc. 76 (1954) 6054.
15. 2 and hydrochloric acid: (c) S.-C. J. Fu, S. M. Birnbaum, and J. P. Greenstein, J. Am. Chem. Soc. 76 (1954) 6054.
16. 2 and hydrochloric acid: (c) S.-C. J. Fu, S. M. Birnbaum, and J. P. Greenstein, J. Am. Chem. Soc. 76 (1954) 6054.
17. 2 and polyhydrogen fluoride:
18. (e) G. A. Olah and J. Welch, Synthesis (1974) 652.
19. (f) G. Lowe and B. V. L. Potter, J. Chem. Soc., Perkin I (1980) 2029.
20. N2 reaction of α-sulfonyloxialkanoate with potassium fluoride:
21. (h) E. Fritz-Langhals and G. Schütz, Tetrahedron Lett. 34 (1993) 293.
22. Diastereoselective halogenation of chiral acetals, see: (a) C. Giordano, G. Castaldi, S. Cavicchioli, and M. Villa, Tetrahedron 45 (1989) 4243. (b) C. Giordano, L. Coppi, and A. Restelli, J. Org. Chem. 55 (1990) 5400 and references cited therein.
23. Diastereoselective halogenation of chiral acetals, see: (a) C. Giordano, G. Castaldi, S. Cavicchioli, and M. Villa, Tetrahedron 45 (1989) 4243. (b) C. Giordano, L. Coppi, and A. Restelli, J. Org. Chem. 55 (1990) 5400 and references cited therein.
24. E. W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, San Diego, CA, 1988, p. 77.
25. R = 15.7 min for major enantiomer of 10c.