Efficient cyclization of ω-oxo-α,β-unsaturated esters using lithium thiolate-initiated Michael-aldol tandem reaction

Tetrahedron Letters

Volumn 40, Issue 38, 1999, Pages 6979-6982

  Ono, Masashi ^a   Nishimura, Katsumi ^a   Nagaoka, Yasuo ^a   Tomioka, Kiyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; LITHIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033578769     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01439-2     Document Type: Article

References (35)

1. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon Press: New York, 1991.
2. Ono, M.; Nishimura, K.; Nagaoka, Y; Tomioka, K. Tetrahedron Lett. 1999, 40, 1509-1512.
3. Annulation-type cyclization has been reported using aluminium thiolate and lithium benzenethiolate-trimethylaluminium. (a) Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274-278.
4. (b) Armstead, D. M.; Danishefsky, S. L. Tetrahedron Lett. 1987, 28, 4959-4962.
5. (c) Levin, J. I. Synth. Commun. 1992, 22, 961-970.
6. (d) Magnus, P.; Miknis, G. F.; Press, N. J.; Grandjean, D.; Taylor, G. M.; Harling, J. J. Am. Chem. Soc. 1997, 119, 6739-6748.
7. Michael-alkylation of 3-bromobut-2-enoate: Little, R. D.; Dawson, J. R. Tetrahedron Lett. 1980, 21, 2609-2612.
8. Michael-initiated cyclization has been extensively studied. Double Michael reaction: (a) Saito, S. J. Syn. Org. Chem. 1992, 50, 316-325.
9. (b) Hagiwara, H. J. Syn. Org. Chem. 1992, 50, 713-725.
10. (c) Uyehara, T.; Shida, N.; Yamamoto, Y. J. Org. Chem. 1992, 57, 3139-3145.
11. (d) Ihara, M.; Makita, K.; Tokunaga, Y; Fukumoto, K. J. Org. Chem. 1994, 59, 6008-6013.
12. (e) Yoshizaki, H.; Tanaka, T.; Yoshii, E.; Koizumi, T.; Takeda, K. Tetrahedron Lett. 1998, 39, 47-50.
13. Michael-alkylation: (f) Fang, C.-L.; Suemune, H.; Sakai, K. J. Org. Chem. 1992, 57, 4300-4303.
14. (g) Enders, D.; Wiedemann, J.; Bettray, W. Synlett 1995, 369-370.
15. Michael-Dieckman reaction: (h) Nugent, W. A; Hobbs Jr., F. W. J. Org. Chem. 1983, 48, 5364-5366.
16. (i) Yamaguchi, M.; Hasebe, K.; Tanaka, S.; Minami, T. Tetrahedron Lett. 1986, 27, 959-962.
17. Baylis-Hillman reaction: (j) Roth, F; Gygax, P.; Frater, G. Tetrahedron Lett. 1992, 33, 1045-1048.
18. (k) Black, G. P.; Dinon, F; Fratucello, S.; Murphy, P. J.; Nielsen, M.; Williams, H. L. Tetrahedron Lett. 1997, 38, 8561-8564.
19. The ω-oxo-α,β-unsaturated esters 1 were prepared by the Wittig reaction of the corresponding dialdehyde equivalents.
20. The ratio of cis to trans of these isomers of 4 was alternatively determined by NMR of the crude product. Other possible two isomers were not detected.
21. The new compounds described herein gave satisfactory analytical and spectroscopic data.
22. Reaction of methyl cyclohexenecarboxylate with lithium benzenethiolate gave stereoselectively cis-phenylsulfanylester, cis-form of Nishimura, K.; Ono, M.; Nagaoka, Y; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975.
23. The coupling constants between each methine protons, J=3.8 Hz for cis-7 and J=9.9 Hz for trans-8, apparently supported the assignment.
24. 2) gave the corresponding hydroxyesters. Five-membered cis-hydroxyester: Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chim. Acta 1987, 70, 1605-1615. Six-membered cis-hydroxyester: Lubineau, A.; Queneau, Y. J. Org. Chem. 1987, 52, 1001-1007.Six-membered frans-hydroxyester: Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743-5754. Seven-membered cis-hydroxyester: Danchet, S.; Bigot, C.; Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1997, 8, 1735-1739.
25. 2) gave the corresponding hydroxyesters. Five-memberedcis-hydroxyester: Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chim. Acta1987, 70, 1605-1615. Six-membered cis-hydroxyester: Lubineau, A.; Queneau, Y. J. Org. Chem. 1987, 52, 1001-1007. Six-membered frans-hydroxyester: Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743-5754. Seven-membered cis-hydroxyester: Danchet, S.; Bigot, C.; Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1997, 8, 1735-1739.
26. 2) gave the corresponding hydroxyesters. Five-memberedcis-hydroxyester: Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chim. Acta1987, 70, 1605-1615. Six-membered cis-hydroxyester: Lubineau, A.; Queneau, Y. J. Org. Chem. 1987, 52, 1001-1007.Six-membered frans-hydroxyester: Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743-5754. Seven-membered cis-hydroxyester: Danchet, S.; Bigot, C.; Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1997, 8, 1735-1739.
27. 2) gave the corresponding hydroxyesters. Five-memberedcis-hydroxyester: Seebach, D.; Roggo, S.; Maetzke, T.; Braunschweiger, H.; Cercus, J.; Krieger, M. Helv. Chim. Acta1987, 70, 1605-1615. Six-membered cis-hydroxyester: Lubineau, A.; Queneau, Y. J. Org. Chem. 1987, 52, 1001-1007.Six-membered frans-hydroxyester: Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743-5754. Seven-membered cis-hydroxyester: Danchet, S.; Bigot, C.; Buisson, D.; Azerad, R. Tetrahedron: Asymmetry 1997, 8, 1735-1739.
28. The cis/trans refers the relationship between the carbons bearing the hydroxy and alkoxycarbonyl groups.
29. The cis-enolate refers the syn orientation of OLi and side chain. Formation of the cis-enolate is tentatively assigned based on the model 9.
30. Protonation has been proposed to take place from a similar conformation. Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T.; Date, T.; Okamura, K.; Inagaki, S. J. Org. Chem. 1991, 56, 6556-6564.
31. (a) Tomioka, K.; Kawasaki, H.; Yasuda, K.; Koga, K. J. Am. Chem. Soc. 1988, 110, 3597-3601.
32. (b) Kim, D.; Kim, H. S. J. Org. Chem. 1987, 52, 4633-4634.
33. The high acidity of benzenethiol is the origin of the equilibrium favoring starting materials.
34. 2) was assigned by analogy based on NMR.
35. 4. Concentration and purification by silica gel column chromatography (hexane/AcOEt=4/1) gave cis-4bb (266 mg, 95%) as a white solid of mp 52-53°C.