The conjugate addition-aldol tandem reaction of α,β-unsaturated esters catalyzed by lithium benzenethiolate

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1509-1512

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ESTER; LITHIUM BENZENETHIOLATE; LITHIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONJUGATE; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033582724     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02664-1     Document Type: Article

References (32)

1. Trost, B. M.; Fleming, I.; Heathcock, C. H. Eds. Comprehensive Organic Synthesis Pergamon Press, New York, 1991.
2. Review for the Lewis acid-promoted aldol reaction, see: (a) Mukaiyama, T. Aldrichimica Acta 1996, 29, 59-76.
3. (b) Ogino, T.; Onozawa, T. J. Synth. Org. Chem. 1998, 56, 71-73.
4. For the recent publications, see: (c) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859-10860.
5. (d) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985-2986.
6. Shioiri, T.; Bohsako, A.; Ando, A. Heterocycles 1996, 42, 93-96.
7. For the review, see: (a) Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. Adv. Carbanion Chem. 1996, 2, 111-146.
8. (b) Shibasaki, M; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1237-1256.
9. For the recent publications, see: (c) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727-1732.
10. (d) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463-466.
11. (e) Hagiwara, E.; Fujii;, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474-2475.
12. For the review, see: (a) Ciganek, E. Org. React. 1997, 51, 201-350.
13. (b) Basavaiah, D.; Rao, P. D.;Hyma, R. S. Tetrahedron 1996, 52, 8001-8062. For the recent publication, see: Brzezinsli, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318.
14. (b) Basavaiah, D.; Rao, P. D.;Hyma, R. S. Tetrahedron 1996, 52, 8001-8062. For the recent publication, see: Brzezinsli, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317-4318.
15. Yura, T.; Iwasawa, N. Mukaiyama, T. Chem. Lett. 1986, 187-190.
16. (a) Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274-278.
17. (b) Levin, J. I. Syn. Commun. 1992, 22, 961-970.
18. The Lewis acid promoted reactions: (a) Suzuki, M.; Kawagishi, T.; Noyori, R. Tetrahedron Lett. 1981, 22, 1809-1812.
19. (b) Barrett, A. G. M.; Kamimura, A. J. Chem. Soc. Chem. Commun. 1995, 1755-1756.
20. (a) Shono, T.; Matsumura, Y.; Kashimura, S.; Hatanaka, K. J. Am. Chem. Soc. 1979, 101, 4752-4753.
21. (b) E. Vedejs, J. B. Campbell, Jr., R. C. Gadwood, J. D. Rodgers, K. L. Spear, Y. Watanabe, J. Org. Chem. 1982, 47, 1534-1546.
22. (a) Watanabe, M.; Shirai, K.; Kumamoto, T. Bull. Chem. Soc. Jpn. 1979, 52, 3318-3320.
23. (b) McCombie, S. W.; Tagat, J. R.; Metz, W. A.; Nazareno, D.; Puar, M. S. Tetrahedron 1993, 46, 8073-8086.
24. The conjugate addition-aldol tandem reaction of acrylates has been reported. Kamimura, A.; Mitsudera, H.; Asano, S.; Kakehi, A.; Noguchi, M. Chem. Commun. 1998, 1095-1096.
25. (a) Nishimura, K.; Ono, T.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975.
26. (b) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144.
27. The new compounds described herein gave satisfactory analytical and spectroscopic data.
28. The antilsyn refers the relationship between C2 and C3 bearing the phenylsulfanyl group.
29. The ratio of anti to syn of these four isomers of 4 were alternatively determined by deoxygenation through treatment with diimidazolylmethane-1-thione and then tributyltinhydride-AIBN to the two diastereomers that were then treated with mCPBA followed by thermal syn-elimination to afford E- and Z-olefins, methyl 2-benzylbut-2-enoate in the same ratio of 74 : 26.
30. The ratio of four isomers 4a was determined by NMR to be 69 : 20 : 8 : 3, corresponding to 89 : 11 for anti- to syn-4a. The stereochemistry around the OH function was determined according to the reported coupling constant (A, D: ca. 5 Hz; B, C: 7-9 Hz). Heathcock, C. H.; Pirrung, M. C.; Sohn, J. E. J. Org. Chem. 1979, 29, 4292-4299. The numbers in parentheses are the diastereomeric ratio based on the C2 and C-OH centers, corresponding to the structures, the most major A to the most minor D. (Formula Presented)
31. 2 = t-Bu; Scheme 5) in 83% yield.
32. 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.