Diastereo- and enantioselective synthesis of 2,3- and 1,2-disubstituted 4-oxophosphonates via asymmetric Michael addition

Tetrahedron

Volumn 53, Issue 38, 1997, Pages 12961-12978

  Enders, Dieter ^a   Wahl, Heiner ^a   Papadopoulos, Kyriakos ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030864546     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00814-4     Document Type: Article

References (36)

1. For some examples see: Enders, D.; Wahl, H.; Papadopoulos, K. Liebigs Ann. 1995, 1177-1184.
2. Minowa, N.; Hirayama, M.; Fukatsu, S. Tetrahedron Lett. 1984, 25, 1147-1150.
3. Ruiz, M.; Ojea, V.; Shapiro, G.; Weber, H.-P. Tetrahedron Lett. 1994, 35, 4551-4554.
4. For asymmetric cis dihydroxylation of phosphonates see for example: Lohray, B. B.; Maji, D. K.; Nandanan, E. Ind. J. Chem. Sect. B 1995, 34, 1023-1025.
5. For the asymmetric synthesis of aminophosphonates see for example: Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M. W.; Blaszczyk, J. Chem. Comm. 1996, 1503-1504.
6. Enders, D.; Eichenauer, H. Angew. Chem. 1976, 88, 579-581. - Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933-2960.
7. Enders, D.; Eichenauer, H. Angew. Chem. 1976, 88, 579-581. - Enders, D.; Eichenauer, H. Chem. Ber. 1979, 112, 2933-2960.
8. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
9. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
10. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
11. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
12. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
13. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
14. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
15. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
16. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
17. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
18. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
19. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
20. Enders, D.; Papadopoulos, K. Tetrahedron Lett. 1983, 24, 4967-4970. - Enders, D.; Rendenbach, B. E. M. Tetrahedron 1986, 42, 2235-2242. - Enders, D.; Papadopoulos, K.; Rendenbach, B. E. M.; Appel, R.; Knoch, F. Tetrahedron Lett. 1986, 72, 3491-3494. - Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223-1227. - Enders, D.; Rendenbach, B. E. M. In Enantioselective Synthesis of Bioregulators in Pesticide Science and Biotechnology; Greengalph, R.; Roberts, T. R. Eds.; Blackwell Scientific Publishers, Oxford, 1987, p. 17. - Enders, D.; Demir, A. S.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1731-1735. - Enders, D.; Demir, A. S.; Puff, H.; Franken, S. Tetrahedron Lett. 1987, 28, 3795-3798. - Enders, D.; Müller, S.; Demir, A. S. Tetrahedron Lett. 1988, 29, 6437-6440. - Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem. 1991, 103, 1676-1678; Angew. Chem Int. Ed. Engl. 1991, 30, 1664-1666. - Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929-1944. - Enders, D.; Papadopoulos, K.; Herdtweck, E. Tetrahedron 1993, 49, 1821-1830. Enders, D.; Bartzen, D. Liebigs Ann. Recueil 1997, 1089-1100.
21. For reviews on the SAMP/RAMP hydrazone method see: Enders. D. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press, Orlando, 1984, Vol. 3B, p. 275. - Enders, D.; Klatt, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A. Ed.; Wiley, New York, 1995, p. 3368.
22. For reviews on the SAMP/RAMP hydrazone method see: Enders. D. In Asymmetric Synthesis; Morrison, J. D. Ed.; Academic Press, Orlando, 1984, Vol. 3B, p. 275. - Enders, D.; Klatt, M. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A. Ed.; Wiley, New York, 1995, p. 3368.
23. ee Values were deduced from the ds values of hydrazones 4.
24. Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1337-1361. - Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1362-1383.
25. Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1337-1361. - Corey, E. J.; Enders, D. Chem. Ber. 1978, 111, 1362-1383.
26. For a short review see: Teulade, M.-P.; Savignac, P. Janssen Chimica Acta 1988, 6, 3 and references cited therein.
27. Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A. Synthesis 1976, 396-398. - Gloyna, D.; Koppel, H.; Henning, H.-G. J. Prakt. Chem. 1974, 316, 832-838.
28. Mikolajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A. Synthesis 1976, 396-398. - Gloyna, D.; Koppel, H.; Henning, H.-G. J. Prakt. Chem. 1974, 316, 832-838.
29. Czekanski, T.; Gross, H.; Costisella, B. J. Prakt. Chem. 1982, 324, 537-544.
30. Papadopoulos, K. Ph. D. Thesis, University of Bonn, 1985.
31. Rotations were measured on the (E)/(Z) isomers. The isomers along the C-N double bond were equilibrated upon heating the hydrazones to 90 to 110°C for 4 h.
32. 13C NMR spectroscopy or analytical HPLC.
33. Resonance of the minor isomers are given. Configurations were not determined.
34. The anti and syn isomers were separated by preparative HPLC.
35. NMR data of the major diastereomer are given and significant chemical shifts of the minor are added in brackets {}.
36. NMR data of both diastereomers are given.