Enantioselective synthesis of (S)-4-methyleneglutamic acid via tandem conjugate addition-elimination under phase-transfer catalytic conditions

Tetrahedron

Volumn 66, Issue 24, 2010, Pages 4326-4329

  Kang, Sukhoon ^a   Shi, Qinghua ^b   Ha, Min Woo ^a   Ku, Jin Mo ^a   Cheng, Maosheng ^b   Jeong, Byeong Seon ^c   Park, Hyeung geun ^a   Jew, Sang sup ^a  

^a Seoul National University   (South Korea)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c Yeungnam University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHYLENEGLUTAMIC ACID; BENZOPHENONE DERIVATIVE; BENZOPHENONE IMINE; GLUTAMIC ACID DERIVATIVE; GLYCINE DERIVATIVE; GLYCINE TERT BUTYL ESTER; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CATALYST; CHIRALITY; CINCHONA; CONJUGATION; CYCLOADDITION; ENANTIOSELECTIVITY; HYDROLYSIS; PHASE TRANSITION; PRIORITY JOURNAL; TANDEM CONJUGATE ADDITION ELIMINATION REACTION;

CINCHONA;

EID: 77953122447     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.034     Document Type: Article

References (29)

1. Done J., and Fowden L. Biochem. J. 51 (1952) 451
2. Zacharius R.M., Pollard J.K., and Steward F.C. J. Am. Chem. Soc. 76 (1954) 1961
3. Tschiersch B. Phytochemistry 1 (1962) 103
4. Blake J., and Fowden L. Biochem. J. 92 (1964) 136
5. Watson R., and Fowden L. Phytochemistry 12 (1973) 617
6. Hatanaka S.-I., and Katayama H. Phytochemistry 14 (1975) 1434
7. Evans C.S., and Bell E.A. Phytochemistry 17 (1978) 1127
8. Shewry P.R., and Fowden L. Phytochemistry 15 (1976) 1981
9. Meier L.K., and Sorensen H. Phytochemistry 18 (1979) 1173
10. Kasai T., Nishitoba T., Shiroshita Y., and Sakamura S. Agric. Biol. Chem. 48 (1984) 2271
11. Powell G.K., and Dekker E.E. Prep. Biochem. 11 (1981) 339
12. Guibé E., Decottignies-LeMaréchal P., Le Maréchal P., and Azerad R. FEBS Lett. 177 (1984) 265
13. Baldwin J.E., Adlington R.M., and Robinson N.G. J. Chem. Soc., Chem. Commun. (1987) 153
14. Moody C.M., and Young D.W. Tetrahedron Lett. 34 (1993) 4667
15. Exquerra J., Pedregal C., Micó I., and Nájera C. Tetrahedron: Asymmetry 5 (1994) 921
16. Dieterich P., and Young D.W. Org. Biomol. Chem. 4 (2006) 1492
17. For our recent review on the cinchona alkaloid-based phase-transfer catalysts for asymmetric synthesis, see:. Jew S.-s., and Park H.-g. Chem. Commun. (2009) 7090
18. For our recent reports on asymmetric phase-transfer catalysis, see:. Yoo M.-S., Jeong B.-S., Lee J.-H., Park H.-g., and Jew S.-s. Org. Lett. 7 (2005) 1129
19. Kim T.-S., Lee Y.-J., Jeong B.-S., Park H.-g., and Jew S.-s. J. Org. Chem. 71 (2006) 8276
20. Lee J., Kim M.-h., Jew S.-s., Park H.-g., and Jeong B.-S. Chem. Commun. (2008) 1932
21. Kim T.-S., Lee Y.-J., Lee K., Jeong B.-S., Park H.-g., and Jew S.-s. Synlett (2009) 671
22. Kim M.-h., Choi S.-H., Lee Y.-J., Lee J., Nahm K., Jeong B.-S., Park H.-g., and Jew S.-s. Chem. Commun. (2009) 782
23. Park Y., Kang S., Lee Y.-J., Kim T.-S., Jeong B.-S., Park H.-g., and Jew S.-s. Org. Lett. 11 (2009) 3738
24. Ramachandran P.V., Madhi S., Bland-Berry L., Reddy M.V.R., and O'Donnell M.J. J. Am. Chem. Soc. 127 (2005) 13450
25. Byun H.-S., Reddy K.C., and Bittman R. Tetrahedron Lett. 35 (1994) 1371
26. O'Donnell M.J., Bennett W.D., and Wu S. J. Am. Chem. Soc. 111 (1989) 2353
27. Lygo B., and Wainwright P.G. Tetrahedron Lett. 38 (1997) 8595
28. Corey E.J., Xu F., and Noe M.C. J. Am. Chem. Soc. 119 (1997) 12414
29. Jew S.-s., Yoo M.-S., Jeong B.-S., and Park H.-g. Org. Lett. 4 (2002) 4245