Enantioselective Dreiding-Schmidt reactions: Asymmetric synthesis and analysis of α-methylene-γ-butyrolactones

Tetrahedron Asymmetry

Volumn 8, Issue 9, 1997, Pages 1411-1429

  Csuk, René ^a   Schröder, Christina ^b   Hutter, Sonja ^b   Mohr, Kristina ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE;

ARTICLE; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342547018     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00166-3     Document Type: Article

References (31)

1. Hoffmann, H. M. R.; Rabe, J., Angew. Chem., Int. Ed. Engl. 1985, 24, 94-116; Hausen, B. M., Deutsch. Apoth. Ztg. 1991, 131, 987-995.
2. Hoffmann, H. M. R.; Rabe, J., Angew. Chem., Int. Ed. Engl. 1985, 24, 94-116; Hausen, B. M., Deutsch. Apoth. Ztg. 1991, 131, 987-995.
3. Kupchan, S. M.; Eakin, M. A.; Thomas, A. M., J. Med. Chem. 1971, 14, 1147-1152.
4. Hutchinson, C. R., J. Org. Chem. 1974, 39, 1854-1858.
5. Iino, Y.; Tanako, A.; Yamashita, K., Agric. Biol. Chem. 1972, 36, 2505-2509.
6. Petragnani, N.; Ferraz, M. C.; Silva, G. V. J., Synthesis 1986, 157-183.
7. Grieco, P. A., Synthesis 1975, 67-82.
8. For an excellent review: Petragnani, N.; Ferraz, H. M.-C.; Silva, G. V. J., Synthesis 1986, 157-183.
9. Enantioselectivity by intermediary diastereoselection using optical pure sulfoxides has been reported to furnish α-methylene-γ-butyrolactones with high ee's, cf Bravo, P.; Resnati, G.; Viani, F., Tetrahedron Lett. 1985, 26, 2913-2916.
10. However, inductions have been observed upon using chiral carbonyl compounds, cf. Csuk, R.; Hugener, M.; Vasella, A., Helv. Chim. Acta 1988, 71, 609-618; Csuk, R.; Glänzer, B. I.; Hu, Z.; Boese, R., Tetrahedron 1994, 50, 1111-1124; Csuk, R.; Fürstner A.; Weidmann, H., J. Carbohydr. Chem. 1987, 6, 459-467.
11. However, inductions have been observed upon using chiral carbonyl compounds, cf. Csuk, R.; Hugener, M.; Vasella, A., Helv. Chim. Acta 1988, 71, 609-618; Csuk, R.; Glänzer, B. I.; Hu, Z.; Boese, R., Tetrahedron 1994, 50, 1111-1124; Csuk, R.; Fürstner A.; Weidmann, H., J. Carbohydr. Chem. 1987, 6, 459-467.
12. However, inductions have been observed upon using chiral carbonyl compounds, cf. Csuk, R.; Hugener, M.; Vasella, A., Helv. Chim. Acta 1988, 71, 609-618; Csuk, R.; Glänzer, B. I.; Hu, Z.; Boese, R., Tetrahedron 1994, 50, 1111-1124; Csuk, R.; Fürstner A.; Weidmann, H., J. Carbohydr. Chem. 1987, 6, 459-467.
13. Reaction of N-mono substituted 2-[(tributylstannyl)methyl]-propenamides with aldehydes in the presence of 4 equiv. of TiCl4 gave, after hydrolysis, α-methylene-γ-butyrolactones with ee's between 3.3-79%, cf. Tanaka, K.; Yoda, H.; Isobe, Y.; Kaji, A., J. Org. Chem. 1986, 51, 1856-1866.
14. Similary to the Gilman-Speeter reaction (Gilman, H.; Specter, M., J. Am. Chem. Soc. 1943, 65, 2255-2256) enantioselectivities between 95-100% have been obtained for the reaction of amino acid derived imines with organozinc reagents, cf. Dembele, Y. A.; Belaud, C.; Hitchock, P.; Villieras, J., Tetrahedron: Asymmetry 1992, 3, 351-354.
15. Similary to the Gilman-Speeter reaction (Gilman, H.; Specter, M., J. Am. Chem. Soc. 1943, 65, 2255-2256) enantioselectivities between 95-100% have been obtained for the reaction of amino acid derived imines with organozinc reagents, cf. Dembele, Y. A.; Belaud, C.; Hitchock, P.; Villieras, J., Tetrahedron: Asymmetry 1992, 3, 351-354.
16. For Dreiding-Schmidt reactions: Öhler, E.; Reininger, K.; Schmidt, U., Angew. Chem., Int. Ed. Engl. 1970, 9, 457-458; Löffler, A.; Pratt, R. J.; Rüesch, H. P.; Dreiding, A. S., Helv. Chim. Acta 1970, 53, 383-403.
17. For Dreiding-Schmidt reactions: Öhler, E.; Reininger, K.; Schmidt, U., Angew. Chem., Int. Ed. Engl. 1970, 9, 457-458; Löffler, A.; Pratt, R. J.; Rüesch, H. P.; Dreiding, A. S., Helv. Chim. Acta 1970, 53, 383-403.
18. For a samarium iodide based approach: Csuk, R.; Höring, U.; Schaade, M., Tetrahedron 1996, 52, 9759-9776.
19. Ameer, F.; Drewes, S. E.; Emslie, N. D.; Kaye, P. T.; Mann, R. L., J. Chem. Soc., Perkin Trans 1 1983, 2293-2295.
20. For the previous use of acrylic amides: Fitt, J. F.; Gschwend, H. W., J. Org. Chem. 1980, 45, 4259-4260.
21. MS spectra and elemental analysis revealed 25 to consist as a 60:40 mixture of 25 and 26 that could not be separated either by distillation or chromatography. The formation of 26 results from a bromine - chlorine substitution during the formation of the acid chloride. To avoid this side reaction attempts were undertaken to synthesize the correponding 2-bromometacrylic bromide by the reaction of 24 with oxalyl dibromide. These reactions, however, did not result in the formation of significant amounts of the desired product but huge deterioration took place.
22. Under these conditions the product contains approx. 40% of 34 (cf. 16). In the following reactions only 28 gave the desired reactions very quickly but 34 was partially recovered.
23. Interestingly enough, neither a halogen exchange reaction occurs nor products resulting from a double addition reaction have been observed.
24. Reiser, O., Nachr. Chem. Tech. Lab. 1996, 44, 612-618 and refs. cited therein.
25. This seems to be due to a minimization of the dipole moments, cf. Oppolzer, W.; Chapuis, C.; Bernadinelli, G., Helv. Chim. Acta 1984, 67, 1397-1401 and Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G., Helv. Chim. Acta 1987, 70, 2201-2214.
26. This seems to be due to a minimization of the dipole moments, cf. Oppolzer, W.; Chapuis, C.; Bernadinelli, G., Helv. Chim. Acta 1984, 67, 1397-1401 and Oppolzer, W.; Poli, G.; Kingma, A. J.; Starkemann, C.; Bernardinelli, G., Helv. Chim. Acta 1987, 70, 2201-2214.
27. Oppolzer, W.; Rodriguez, I.; Blagg, J.; Bernardinelli, G., Helv. Chim. Acta 1989, 72, 123-130.
28. 20.
29. Löffler, A.; Pratt, R. D.; Pucknat, J.; Gelbart, G.; Dreiding, A. S., Chimia 1969, 23, 413-416.
30. Xu, L.-H.; Kündig, E. P., Helv. Chim. Acta 1994, 77, 1480-1484.
31. Villieras, J.; Rambaud, U., Synthesis 1982, 924-926.