Zn(II)/amine-catalyzed coupling reaction of alkylidenemalonates with propargyl alcohol: A one-pot synthesis of methylenetetrahydrofurans

Organic Letters

Volumn 6, Issue 12, 2004, Pages 2015-2017

  Nakamura, Masaharu ^a,b   Liang, Chungen ^b   Nakamura, Eiichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; AMINE; MALONIC ACID DERIVATIVE; METAL; TETRAHYDROFURAN DERIVATIVE; TRIETHYLAMINE; TRIFLUOROMETHANESULFONIC ACID; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; MICHAEL ADDITION;

EID: 3042713083     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0493554     Document Type: Article

References (26)

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15. Selected examples of the addition of a carbonyl compound or related enolate species to unactivated alkynes or alkenes: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. (b) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (c) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790. (d) Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-94. (e) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y., Taguchi, T. J. Org. Chem. 1998, 63, 9470, (f) Tsukada, N.; Yamamoto, Y. Angev. Chem., Int. Ed. Engl. 1997, 36, 2477-2480.
16. Selected examples of the addition of a carbonyl compound or related enolate species to unactivated alkynes or alkenes: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. (b) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (c) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790. (d) Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-94. (e) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y., Taguchi, T. J. Org. Chem. 1998, 63, 9470, (f) Tsukada, N.; Yamamoto, Y. Angev. Chem., Int. Ed. Engl. 1997, 36, 2477-2480.
17. Selected examples of the addition of a carbonyl compound or related enolate species to unactivated alkynes or alkenes: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. (b) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (c) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790. (d) Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-94. (e) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y., Taguchi, T. J. Org. Chem. 1998, 63, 9470, (f) Tsukada, N.; Yamamoto, Y. Angev. Chem., Int. Ed. Engl. 1997, 36, 2477-2480.
18. Selected examples of the addition of a carbonyl compound or related enolate species to unactivated alkynes or alkenes: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. (b) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (c) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790. (d) Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-94. (e) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y., Taguchi, T. J. Org. Chem. 1998, 63, 9470, (f) Tsukada, N.; Yamamoto, Y. Angev. Chem., Int. Ed. Engl. 1997, 36, 2477-2480.
19. Selected examples of the addition of a carbonyl compound or related enolate species to unactivated alkynes or alkenes: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. (b) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (c) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790. (d) Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-94. (e) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y., Taguchi, T. J. Org. Chem. 1998, 63, 9470, (f) Tsukada, N.; Yamamoto, Y. Angev. Chem., Int. Ed. Engl. 1997, 36, 2477-2480.
20. Selected examples of the addition of a carbonyl compound or related enolate species to unactivated alkynes or alkenes: (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527. (b) Karoyan, P.; Quancard, J.; Vaissermann, J.; Chassaing, G. J. Org. Chem. 2003, 68, 2256-2265. (c) Arisawa, M.; Akamatsu, K.; Yamaguchi, M. Org. Lett. 2001, 3, 789-790. (d) Lorthiois, E.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 89-94. (e) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y., Taguchi, T. J. Org. Chem. 1998, 63, 9470, (f) Tsukada, N.; Yamamoto, Y. Angev. Chem., Int. Ed. Engl. 1997, 36, 2477-2480.
21. 2, reflux, 15 h), 27% yield (methanol, reflux, 15 h), 42% yield (toluene, 80°C, 15 h).
22. Similar results were obtained with NaH and BuLi as base: 2a was obtained in 77% yield (THF, reflux, 15 h) and in 99% yield (THF, reflux, 15 h).
23. 3.
24. 2O. After removal of solvent, purification with silica gel chromatography gave 2a as a colorless liquid (0.28 g, 93% yield).
25. 1H NMR analyses of the aliquots of the reaction mixture in the course of the addition/cyclization reaction, the isomerization of 1j is much faster than the production of 2j under the reaction conditions. The assignment of the stereochemistry of the compounds was reported in ref 4a.
26. "ZnOTf" is a possible counter cation, and it could be solvated by propargyl alcohol in the reaction system.