New results on the stereoselective alkylations of malic acid derivatives supported by molecular modeling

Helvetica Chimica Acta

Volumn 85, Issue 12, 2002, Pages 4216-4229

  Sefkow, Michael ^a   Koch, Andreas ^a   Kleinpeter, Erich ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; BENZENE; ESTERS;

STEREOSELECTIVITY;

STEREOCHEMISTRY;

1,3 DIOXOLANE DERIVATIVE; MALIC ACID DERIVATIVE;

AB INITIO CALCULATION; ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; LOW TEMPERATURE; MOLECULAR MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0036964912     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200290007     Document Type: Article

References (21)

1. D. C. Ayres, J. D. Loike, 'Lignans, Chemical, Biological and Clinical Properties', Cambridge University Press, Cambridge, 1990.
2. S. Tandon, R. P. Rastogi, Phytochemistry 1976, 15, 1789.
3. R. S. Ward, Nat. Prod. Rep. 1999, 16, 75 and other reviews of this series.
4. a) M. Sefkow, J. Org. Chem. 2001, 66, 2342;
5. b) M. Sefkow, A. Kelling, U. Schilde, Tetrahedron Lett. 2001, 5101;
6. c) M. Sefkow, Tetrahedron: Asymmetry 2001, 12, 987.
7. a) D. Seebach, D. Wasmuth, Helv. Chim. Acta 1980, 63, 197;
8. b) D. Seebach, J. Aebi, D. Wasmuth, Org. Synth. Collect. Vol. VII 1990, 153.
9. D. Seebach, R. Naef, G. Calderari, Tetrahedron 1984, 40, 1313.
10. J. Gawroński, K. Gawrońska, 'Tartaric and Malic Acid in Synthesis', John Wiley, New York, 1999.
11. R. W. Dugger, J. L. Ralbovsky, D. Bryant, J. Commander, S. S. Massett, N. A. Sage, J. R. Selvidio, Tetrahedron Lett. 1992, 33, 6763.
12. B. H. Norman, M. L. Morris, Tetrahedron Lett. 1992, 33, 6803.
13. C. H. Kuo, A. J. Robichaud, D. J. Rew, J. D. Bergstrom, G. D. Berger, Bioorg. Med. Chem. Lett. 1994, 4, 1591.
14. Z.-Q. Tain, B. B. Brown, D. P. Mack, C. A. Hutton, P. A. Bartlett, J. Org. Chem. 1997, 62, 514.
15. L. J. Mathias, Synthesis 1976, 561.
16. Gaussian 98, Revision A.11.3, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2002.
17. J. E. Baldwin, L. I. Kruse, J. Chem. Soc., Chem. Commun. 1977, 233; H. O. House, W. V. Phillips, T. S. B. Sayer, C.-C. Yau, J. Org. Chem. 1978, 43, 700.
18. J. E. Baldwin, L. I. Kruse, J. Chem. Soc., Chem. Commun. 1977, 233; H. O. House, W. V. Phillips, T. S. B. Sayer, C.-C. Yau, J. Org. Chem. 1978, 43, 700.
19. D. D. Perrin, W. L. F. Armarego, 'Purification of Laboratory Chemicals', 3rd edn., Pergamon Press, 1988.
20. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
21. SYBYL 6.8, Tripos Inc., 1699 South Hanley Road, St Louis, MO, 2001.