Bidentate chelation-controlled asymmetric synthesis of α-hydroxy esters based on the glycolate enolate alkylation

Tetrahedron Letters

Volumn 41, Issue 11, 2000, Pages 1793-1796

  Jung, Ju Eun ^a   Ho, Hyunsoon ^a   Kim, Hee Doo ^a  

^a Sookmyung Women's University   (South Korea)

Author keywords

Alkylation; Asymmetric synthesis; Chelation; Hydroxy acid and derivatives

Indexed keywords

ESTER DERIVATIVE; GLYCOLIC ACID;

ALKYLATION; ARTICLE; CHELATION; CHEMICAL REACTION; ESTERIFICATION; SYNTHESIS;

EID: 0000594896     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00031-9     Document Type: Article

References (17)

1. Coppola, G. M.; Schuster, H. F. Hydroxy Acids in Enantioselective Syntheses; VCH: Weinheim, 1997.
2. Hanessian, S. Total Synthesis of Natural Products. The Chiron Approach; Pergamon Press: New York, 1983; Chapter 2.
3. Pansare, S. V.; Ravi, R. G. Tetrahedron 1998, 54, 14549-14564 and references cited therein.
4. Frater, G. Y.; Muller, U.; Gunther, W. Tetrahedron Lett. 1981, 22, 4221-4224.
5. Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746-3748.
6. Ludwig, J. W.; Newcomb, M.; Bergbreiter, D. E. Tetrahedron Lett. 1986, 27, 2731-2734.
7. d'Angelo, J.; Pages, O.; Maddaluno, J.; Dumas, F.; Revial, G. Tetrahedron Lett. 1983, 24, 5869-5872.
8. Helmchen, G.; Wierzchowski, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 60-61.
9. Kelly, T. R.; Arvanitis, A. Tetrahedron Lett. 1984, 25, 39-42.
10. Enomoto, M.; Ito, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1985, 26, 1343-1344.
11. Schimid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Philips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056-4058.
12. Sugimura, H.; Watanabe, T. Synlett 1994, 175-176.
13. Sato, F.; Kobayashi, Y.; Takahashi, O.; Chiba, T.; Takeda, Y.; Kusakabe, M. J. Chem. Soc., Chem. Commun. 1985, 1636-1638.
14. Schimid, C. R.; Bryant, J. D. Org. Synth. Coll. Vol. IX. 1998, 450-453; Hubschwerlen, C.; Specklin, J.-L.; Higelin, J. ibid, 454-456.
15. Schimid, C. R.; Bryant, J. D. Org. Synth. Coll. Vol. IX. 1998, 450-453; Hubschwerlen, C.; Specklin, J.-L.; Higelin, J. ibid, 454-456.
16. Nakamura, K.; Inoue, K.; Ushio, K.; Oka, S.; Ohno, A. J. Org. Chem. 1988, 53, 2589-2593.
17. Chikashita, H.; Nikaya, T.; Uemura, H.; Itoh, K. Bull. Chem. Soc. Jpn. 1989, 62, 2121-2123.