Aldol reactions of unsubstituted β-lactams. Studies of a β-glycine enolate equivalent

Heterocycles

Volumn 62, Issue , 2004, Pages 167-172

  Williams, David R ^a   Donnell, Andrew F ^a   Kammler, David C ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZETIDINE DERIVATIVE; BETA AMINO ESTER; BETA GLYCINE ENOLATE; BETA LACTAM; ESTER DERIVATIVE; GLYCINE DERIVATIVE; LITHIUM; N (4 METHOXYBENZYLOXY)AZETIDIN 2 ONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346459988     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. 'The Organic Chemistry of β-Lactams,' ed. by G. I. Georg, VCH, New York, 1993; 'The Chemistry of β-Lactams,' ed. by M. I. Page, Blackie Academic and Professional, New York, 1992.
2. 'The Organic Chemistry of β-Lactams,' ed. by G. I. Georg, VCH, New York, 1993; 'The Chemistry of β-Lactams,' ed. by M. I. Page, Blackie Academic and Professional, New York, 1992.
3. Reviews: P. A. Magriotis, Angew. Chem., Int. Ed., 2001, 40, 4377; N. De Kimpe, T. Y. Zhang, L. D. Hatfield, J. T. B. H. Jastrzebski, G. Van Koten, J. Parrick, and L. K. Mehta, 'Comprehensive Heterocyclic Chemistry II,' Vol. 1B, ed. by A. R. Katritzky, C. W. Rees, E. F. V. Scriven, and A. Padwa, Elsevier Science, Inc., New York, 1993, pp. 507-720; L. Ghosez and J. Marchand-Brynaert, 'Comprehensive Organic Synthesis,' Vol. 5, ed. by B. M. Trost, I. Fleming, and L. A. Paquette, Pergamon Press, New York, 1991, pp. 85-122.
4. Reviews: P. A. Magriotis, Angew. Chem., Int. Ed., 2001, 40, 4377; N. De Kimpe, T. Y. Zhang, L. D. Hatfield, J. T. B. H. Jastrzebski, G. Van Koten, J. Parrick, and L. K. Mehta, 'Comprehensive Heterocyclic Chemistry II,' Vol. 1B, ed. by A. R. Katritzky, C. W. Rees, E. F. V. Scriven, and A. Padwa, Elsevier Science, Inc., New York, 1993, pp. 507-720; L. Ghosez and J. Marchand-Brynaert, 'Comprehensive Organic Synthesis,' Vol. 5, ed. by B. M. Trost, I. Fleming, and L. A. Paquette, Pergamon Press, New York, 1991, pp. 85-122.
5. Reviews: P. A. Magriotis, Angew. Chem., Int. Ed., 2001, 40, 4377; N. De Kimpe, T. Y. Zhang, L. D. Hatfield, J. T. B. H. Jastrzebski, G. Van Koten, J. Parrick, and L. K. Mehta, 'Comprehensive Heterocyclic Chemistry II,' Vol. 1B, ed. by A. R. Katritzky, C. W. Rees, E. F. V. Scriven, and A. Padwa, Elsevier Science, Inc., New York, 1993, pp. 507-720; L. Ghosez and J. Marchand-Brynaert, 'Comprehensive Organic Synthesis,' Vol. 5, ed. by B. M. Trost, I. Fleming, and L. A. Paquette, Pergamon Press, New York, 1991, pp. 85-122.
6. Reviews: I. Ojima and F. Delaloge, Chem. Soc. Rev., 1997, 26, 377; C. Palomo, J. M. Aizpurua, I. Ganboa, and M. Oiarbide, Synlett, 2001, 1813; B. Alcaide and P. Almendros, Synlett, 2002, 381.
7. Reviews: I. Ojima and F. Delaloge, Chem. Soc. Rev., 1997, 26, 377; C. Palomo, J. M. Aizpurua, I. Ganboa, and M. Oiarbide, Synlett, 2001, 1813; B. Alcaide and P. Almendros, Synlett, 2002, 381.
8. Reviews: I. Ojima and F. Delaloge, Chem. Soc. Rev., 1997, 26, 377; C. Palomo, J. M. Aizpurua, I. Ganboa, and M. Oiarbide, Synlett, 2001, 1813; B. Alcaide and P. Almendros, Synlett, 2002, 381.
9. D. R. Williams and S.-Y. Sit, J. Org. Chem., 1982, 47, 2846; D. R. Williams, M. L. Bremmer, D. L. Brown, and J. D'Antuono, J. Org. Chem., 1985, 50, 2807; D. R. Williams and R. A. Turske, Org. Lett., 2000, 2, 3217.
10. D. R. Williams and S.-Y. Sit, J. Org. Chem., 1982, 47, 2846; D. R. Williams, M. L. Bremmer, D. L. Brown, and J. D'Antuono, J. Org. Chem., 1985, 50, 2807; D. R. Williams and R. A. Turske, Org. Lett., 2000, 2, 3217.
11. D. R. Williams and S.-Y. Sit, J. Org. Chem., 1982, 47, 2846; D. R. Williams, M. L. Bremmer, D. L. Brown, and J. D'Antuono, J. Org. Chem., 1985, 50, 2807; D. R. Williams and R. A. Turske, Org. Lett., 2000, 2, 3217.
12. 2, 0 °C, 95% → 2) NaH, DMF, 0 °C to 60 °C, 53% 1
13. F. A. Bouffard, D. B. R. Johnston, and B. G. Christensen, J. Org. Chem., 1980, 45, 1130; see also F. A. Bouffard and T. N. Salzmann, Tetrahedron Lett., 1985, 26, 6285 and references therein.
14. F. A. Bouffard, D. B. R. Johnston, and B. G. Christensen, J. Org. Chem., 1980, 45, 1130; see also F. A. Bouffard and T. N. Salzmann, Tetrahedron Lett., 1985, 26, 6285 and references therein.
15. Asymmetry at C-4 of the β-lactam substrate directs enolate facial selectivity in these cases. I. Ojima and Y. Pei, Tetrahedron Lett., 1990, 31, 977; E. J. Thomas and A. C. Williams, J. Chem. Soc., Perkin Trans. 1, 1995, 351; B. J. Kim, Y. S. Park, and P. Beak, J. Org. Chem., 1999, 64, 1705.
16. Asymmetry at C-4 of the β-lactam substrate directs enolate facial selectivity in these cases. I. Ojima and Y. Pei, Tetrahedron Lett., 1990, 31, 977; E. J. Thomas and A. C. Williams, J. Chem. Soc., Perkin Trans. 1, 1995, 351; B. J. Kim, Y. S. Park, and P. Beak, J. Org. Chem., 1999, 64, 1705.
17. Asymmetry at C-4 of the β-lactam substrate directs enolate facial selectivity in these cases. I. Ojima and Y. Pei, Tetrahedron Lett., 1990, 31, 977; E. J. Thomas and A. C. Williams, J. Chem. Soc., Perkin Trans. 1, 1995, 351; B. J. Kim, Y. S. Park, and P. Beak, J. Org. Chem., 1999, 64, 1705.
18. For an overview: M. J. Miller, Acc. Chem. Res., 1986, 19, 49.
19. 2O at -78 °C. Decomposition resulted when solutions of enolate were warmed from -78 °C to -40 °C. We tentatively suggest formation of dione (8) (1:1 mixture of isomers) via dimerization of the intermediate ketene as a principle pathway. Diagram presented. Similar ratios of anti:syn products were obtained following the addition of 12-crown-4 to solutions of lithium enolate. The latter observation offers support for the open transition state hypothesis.
20. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092.
21. D. R. Williams, P. D. Lowder, and Y.-G. Gu, Tetrahedron Lett., 1997, 38, 327; D. R. Williams, P. D. Lowder, and Y.-G. Gu, Tetrahedron Lett., 2000, 41, 9397.
22. D. R. Williams, P. D. Lowder, and Y.-G. Gu, Tetrahedron Lett., 1997, 38, 327; D. R. Williams, P. D. Lowder, and Y.-G. Gu, Tetrahedron Lett., 2000, 41, 9397.