Additions of silyl enol ethers to β-formyl esters - A chelate-controlled synthesis of the pheromone (+)-eldanolide

Liebigs Annales

Volumn , Issue 2, 1996, Pages 259-263

  Angert, Hubert ^a   Czerwonka, Regina ^a   Reißig, Hans Ulrich ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

(+) Eldanolide; Chelate control; Mukaiyama reaction; Silyl enol ethers; Formyl esters

Indexed keywords

EID: 33748912167     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960216     Document Type: Article

References (31)

1. H. Angert, Dissertation, Technische Universität Dresden, 1995.
2. [2a] T. Kunz, H.-U. Reißig, Angew. Chem. 1988, 100, 297-298;
3. Angew. Chem. Int. Ed. Engl. 1988, 27, 268-270.
4. [2b] T. Kunz, A. Janowitz, H.-U. Reißig, Chem. Ber. 1989, 122, 2165-2175.
5. [3a] A. Janowitz, T. Kunz, G. Handke, H.-U. Reißig, Synlett 1989, 24-25.
6. [3b] H.-U. Reißig, H. Angert, T. Kunz, A. Janowitz, G. Handke, E. Bruce-Adjei, J. Org. Chem. 1993, 58, 6280-6285.
7. Synthesis of 1: E. Kunkel, I. Reichelt, H.-U. Reißig, Liebigs Ann. Chem. 1984, 802-819;
8. T. Kunz, A. Janowitz, H.-U. Reißig, Synthesis 1990, 43-47;
9. H.-U. Reißig, I. Reichelt, T. Kunz, Org. Synth. 1992, 71, 189-199.
10. H. Angert, T. Kunz, H.-U. Reißig, Tetrahedron 1992, 48, 5681-5690. See references in this publication for stereocontrolled and chelate-controlled Mukaiyama reactions.
11. In our earlier experiments we employed coned, hydrochloric acid for the workup which may cause some cis→trans equilibration. Therefore, we now prefer 50% aqueous sulfuric acid which does not equilibrate the lactones.
12. M. Cherest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 2199-2204;
13. N. T. Anh, Top. Curr. Chem. 1980, 88, 145-162.
14. For a recent example exploiting this effect in a stereoselective intramolecular Diels-Alder reaction see: J. Schnaubelt, H.-U. Reißig, Synlett 1995, 452-454.
15. R. F. Childs, D. L. Mulholland, A. Nixon, Can. J. Chem. 1982, 60, 801-808;
16. P. Laszlo, M. Teston, J. Am. Chem. Soc. 1990, 112, 8750-8754, and references cited therein.
17. [1]. In a recent publication on Mukaiyama reactions a surprisingly high dependency of the diastereoselectivity on the silyl enol ether α-substituents was reported without explanation: D. A. Evans, M. J. Dart, J. L. Duffy, M. G. Yang, A. B. Livingston, J. Am. Chem. Soc. 1995, 117, 6619-6620. The Mukaiyama reaction of silyl enol ethers usually proceeds via an acyclic transition state with respect to the enol and the aldehyde moiety, and titanium enolates are generally not involved.
18. For a more detailed discussion of this matter and relevant literature see: H. Angert, R. Schumacher, H.-U. Reißig, Chem. Ber. submitted (CB 95156).
19. J. P. Vigneron, R. Mèric, M. Larcheveque, A. Debal, J. Y. Lallemand, G. Kunesch, P. Zagatti, M. Gallois, Tetrahedron 1984, 40, 3521-3529.
20. P. R. Atkinson, J. Ent. Soc. Sth. Afr. 1980, 43, 171.
21. For some recent syntheses of optically active eldanolide: [13a] H. Paulsen, D. Hoppe, Tetrahedron 1992, 48, 5667-5670, and references cited therein.
22. [13b] Y. Suzuki, W. Mori, H. Ishizone, K. Naito, T. Honda, Tetrahedron Lett. 1992, 33, 4931-4932.
23. [13c] T. Ebata, K. Matsumoto, H. Yoshikoshi, K. Koseki, H. Kawakami, K. Okano, H. Matsushita, Heterocycles 1993, 36, 1017-1026.
24. [13d] T. Honda, S.-i. Yamane, K. Naito, Y. Suzuki, Heterocycles 1994, 37, 515-521.
25. E. Bruce-Adjei, Diplomarbeit, Technische Hochschule Darmstadt, 1990.
26. We also tried to employ the barium reagent prepared according to H. Yamamoto from prenyl chloride as an equivalent for C (A. Yanagisawa, S. Habaue, H. Yamamoto, J. Am. Chem. Soc. 1991, 113, 8955-8956;
27. [1]).
28. A. Bernardi, S. Cardani, T. Pilati, G. Poli, C. Scolastico, R. Villa, J. Org. Chem. 1988, 53, 1600-1607;
29. A. Bernardi, S. Cardani, G. Poli, C. Scolastico, J. Org. Chem. 1986, 51, 5041-5043. An acceptable yield of (S)-1 was only achieved when the thioacetal resulting after the cleavage of the chiral auxiliary was isolated and purified before deprotection of the thioacetal moiety.
30. For a related example see: S. A. Popov, A. V. Rukavishnikov, A. V. Tkachev, Synthesis 1992, 783-786.
31. M. Tsukayama, M. Kikuchi, Y. Kawamura, Heterocycles 1994, 38, 1487-1490.