Synthetic Application of Et3GeNa/LnCl3: Stereoselective Aldol Condensation of Ketones and Amides

Synlett

Volumn 1996, Issue 5, 1996, Pages 445-446

  Yokoyama, Yasuo ^a   Mochida, Kunio ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002662950     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5460     Document Type: Article

References (15)

1. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
2. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
3. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
4. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
5. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
6. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
7. For some examples: (a) Raimudo, B. C.; Heathcock, C. H. Synlett 1995, 1213. (b) Boeckman, R. K.; Johnson, A. T.; Musslemam, R. A. Tetrahedron Lett. 1994, 35, 8521. (c) Ganesan, K.; Brown, H. C. J. Org. Chem. 1994, 59, 2336.; 7346 and cited therein. For some reviews: (d) Heathcock C. H. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: New York, 1992. (e) ibid. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Chapter 2. (f) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
8. Yokoyama Y.; Mochida K. J. Organomet. Chem. 1995, 499, C4.
9. For some examples of synthesis of lanthanoid enolate: (a) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (b) Molander, G. A. Chem. Rev. 1992, 92, 29 and cited therein. (c) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904 and cited therein.
10. For some examples of synthesis of lanthanoid enolate: (a) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (b) Molander, G. A. Chem. Rev. 1992, 92, 29 and cited therein. (c) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904 and cited therein.
11. For some examples of synthesis of lanthanoid enolate: (a) Fukuzawa, S.; Tsuchimoto, T.; Kanai, T. Bull. Chem. Soc. Jpn. 1994, 67, 2227. (b) Molander, G. A. Chem. Rev. 1992, 92, 29 and cited therein. (c) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904 and cited therein.
12. 1H-NMR(300 MHz) analysis. Vinyl protons of Z- and E-diastereomer were observed as quartets in 4.52 ppm (J=6.54 Hz) and 4.60 ppm (J=6.90 Hz). These values agreed with the data of the literature. See: Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
13. Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
14. Bulten E. J.; Noltes J. G. Tetrahedron Lett. 1967, 1443; 1966, 4389.
15. Bulten E. J.; Noltes J. G. Tetrahedron Lett. 1967, 1443; 1966, 4389.