syn-Selective boron mediated aldol condensations for the asymmetric synthesis of β-hydroxy-α-amino acids

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5963-5966

  Caddick, S ^a   Parr, N J ^a   Pritchard, M C ^b  

^a Sch Chem   (United Kingdom)

^b Parke Davis NRC   (United Kingdom)

Author keywords

Aldol; Asymmetric synthesis; Boron; Glycine enolates; Imidazolidinone; hydroxy amino acids

Indexed keywords

ALDEHYDE; ALPHA AMINO ACID; BORON; GLYCINE;

ACYLATION; AMINO ACID SYNTHESIS; ARTICLE; CATALYST; CHEMICAL STRUCTURE; DIPOLE; HYDROGENATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REPRODUCIBILITY; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0034730017     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00734-6     Document Type: Article

References (26)

1. Nakasuka, T.; Miwa, T.; Mukaiyama, T. Chem. Lett. 1981, 279. Nakasuka, T.; Miwa, T.; Mukaiyama, T. Chem. Lett. 1982, 145.
2. Nakasuka, T.; Miwa, T.; Mukaiyama, T. Chem. Lett. 1981, 279. Nakasuka, T.; Miwa, T.; Mukaiyama, T. Chem. Lett. 1982, 145.
3. Sykes, R. B. Nature 1981, 19, 49. Cimarusti, C. M.; Sykes, R. B. Chem. In Brit. 1983, 302; Miller, M. J. Acc. Chem. Res. 1986, 19, 49.
4. Sykes, R. B. Nature 1981, 19, 49. Cimarusti, C. M.; Sykes, R. B. Chem. In Brit. 1983, 302; Miller, M. J. Acc. Chem. Res. 1986, 19, 49.
5. Sykes, R. B. Nature 1981, 19, 49. Cimarusti, C. M.; Sykes, R. B. Chem. In Brit. 1983, 302; Miller, M. J. Acc. Chem. Res. 1986, 19, 49.
6. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
7. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
8. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
9. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
10. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
11. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
12. Shanzer, A.; Somekh, L.; Butina, B. J. Org. Chem. 1979, 44, 3967. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron Lett. 1984, 25, 4693. Gunati, G.; Banfi, L.; Narisano, E. Tetrahedron Lett. 1985, 26, 3517. Guanti, G.; Banfi, L.; Narisano, E.; Scolastico, C. Tetrahedron 1988, 44, 3671. Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 409. Kazmaier, U.; Grandel, R. J. Org. Chem. 1998, 1833.
13. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497. Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S.; Watkin, D. J.; Williams, D. J. Tetrahedron 1998, 54, 6089. Righi, G.; Rumboldt, G.; Bonini, C. Tetrahedron 1995, 51, 13401. Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malloy, M. F.; Gougoutas, J. Z. Synlett. 1998, 664. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
14. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497. Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S.; Watkin, D. J.; Williams, D. J. Tetrahedron 1998, 54, 6089. Righi, G.; Rumboldt, G.; Bonini, C. Tetrahedron 1995, 51, 13401. Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malloy, M. F.; Gougoutas, J. Z. Synlett. 1998, 664. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
15. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497. Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S.; Watkin, D. J.; Williams, D. J. Tetrahedron 1998, 54, 6089. Righi, G.; Rumboldt, G.; Bonini, C. Tetrahedron 1995, 51, 13401. Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malloy, M. F.; Gougoutas, J. Z. Synlett. 1998, 664. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
16. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497. Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S.; Watkin, D. J.; Williams, D. J. Tetrahedron 1998, 54, 6089. Righi, G.; Rumboldt, G.; Bonini, C. Tetrahedron 1995, 51, 13401. Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malloy, M. F.; Gougoutas, J. Z. Synlett. 1998, 664. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
17. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497. Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S.; Watkin, D. J.; Williams, D. J. Tetrahedron 1998, 54, 6089. Righi, G.; Rumboldt, G.; Bonini, C. Tetrahedron 1995, 51, 13401. Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malloy, M. F.; Gougoutas, J. Z. Synlett. 1998, 664. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
18. Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757. Bold, G.; Duthaler, R. O.; Riediker, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 497. Alker, D.; Hamblett, G.; Harwood, L. M.; Robertson, S.; Watkin, D. J.; Williams, D. J. Tetrahedron 1998, 54, 6089. Righi, G.; Rumboldt, G.; Bonini, C. Tetrahedron 1995, 51, 13401. Iwanowicz, E. J.; Blomgren, P.; Cheng, P. T. W.; Smith, K.; Lau, W. F.; Pan, Y. Y.; Gu, H. H.; Malloy, M. F.; Gougoutas, J. Z. Synlett. 1998, 664. Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409.
19. For recent related α-amino-acid syntheses, see: Guillena, G.; Najera, C. Tetrahedron: Asymmetry 1998, 9, 3935. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Tetrahedron Lett. 1997, 38, 6953. Myers, A. G.; Gleason, J. L. Org. Synth. 1999, 76, 57.
20. For recent related α-amino-acid syntheses, see: Guillena, G.; Najera, C. Tetrahedron: Asymmetry 1998, 9, 3935. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Tetrahedron Lett. 1997, 38, 6953. Myers, A. G.; Gleason, J. L. Org. Synth. 1999, 76, 57.
21. For recent related α-amino-acid syntheses, see: Guillena, G.; Najera, C. Tetrahedron: Asymmetry 1998, 9, 3935. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Tetrahedron Lett. 1997, 38, 6953. Myers, A. G.; Gleason, J. L. Org. Synth. 1999, 76, 57.
22. Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 44, 4294.
23. Drewes, S. E.; Malissar, D. G. S.; Roos, G. H. P. Chem. Ber. 1993, 126, 2663, and references cited therein.
24. Kubo, A.; Kubota, H.; Takahashi, M.; Nunami, K. J. Org. Chem. 1997, 62, 5830.
25. Laib, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709.
26. All compounds gave spectroscopic data and microanalyses or high resolution mass spectra consistent with their structures.