Asymmetric synthesis of 3,4-dihydrocoumarins by rhodium-catalyzed reaction of 3-(2-hydroxyphenyl)cyclobutanones

Journal of the American Chemical Society

Volumn 129, Issue 40, 2007, Pages 12086-12087

  Matsuda, Takanori ^a   Shigeno, Masanori ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 HYDROXYPHENYL)CYCLOBUTANONE DERIVATIVE; 3,4 DIHYDROCOUMARIN DERIVATIVE; CARBON; CARBONYL DERIVATIVE; COUMARIN DERIVATIVE; CYCLOBUTANONE DERIVATIVE; DEUTERIUM; ESTER; LACTONE DERIVATIVE; METAL; RHODIUM; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATION; CROSS COUPLING REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; RING OPENING;

EID: 35048874634     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075141g     Document Type: Article

References (35)

1. Reviews: (a) Murakami, M.; Ito, Y. Top. Organomet. Chem. 1999, 3, 97.
2. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
3. (c) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610.
4. (d) Kondo, T.; Mitsudo, T. Chem. Lett. 2005, 34, 1462.
5. Recent examples: (a) Ikeda, S.; Suzuki, K.; Odashima, K. Chem. Commun. 2006, 457.
6. (b) Trost, B. M.; Xie, J. J. Am. Chem. Soc. 2006, 128, 6044.
7. (c) Wender, P. A.; Deschamps, N. M.; Sun, R. Angew. Chem., Int. Ed. 2006, 45, 3957.
8. (d) Shukla, P.; Cheng, C.-H. Org. Lett. 2006, 8, 2867.
9. (e) Tobisu, M.; Kita, Y.; Chatani, N. J. Am. Chem. Soc. 2006, 128, 8152.
10. (f) Nakano, M.; Satoh, T.; Miura, M. J. Org. Chem. 2006, 71, 8309.
11. (g) Murakami, M.; Ashida, S. Chem. Commun. 2006, 4599.
12. (h) Yamamoto, Y.; Kuwabara, S.; Hayashi, H.; Nishiyama, H. Adv. Synth. Catal. 2006, 348, 2493.
13. (i) Nakao, Y.; Yada, A.; Ebata, S.; Hiyama, T. J. Am. Chem. Soc. 2007, 129, 2428.
14. (j) Kondo, T.; Niimi, M.; Nomura, M.; Wada, K.; Mitsudo, T. Tetrahedron Lett. 2007, 48, 2837.
15. Matsuda, T.; Shigeno, M.; Makino, M.; Murakami, M. Org. Lett. 2006, 8, 3379.
16. Matsuda, T.; Shigeno, M.; Maruyama, Y.; Murakami, M. Chem. Lett. 2007, 36, 744.
17. Murakami, M.; Tsuruta, T.; Ito, Y. Angew. Chem., Int. Ed. 2000, 39, 2484.
18. For a leading example of enantioselective carbon-carbon bond cleavage reaction of cyclobutanolates, see: Matsumura, S.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2003, 125, 8862.
19. Cyclobutanones 1 were prepared from the corresponding salicylaldehyde derivatives. See Supporting Information for details.
20. For another example of catalytic asymmetric synthesis of 2a, see: Dong, C.; Alper, H. J. Org. Chem. 2004, 69, 5011.
21. Loiodice, F.; Longo, A.; Bianco, P.; Tortorella, V. Tetrahedron: Asymmetry 1995, 6, 1001.
22. 1H NMR spectra of cyclobutanones 1d-j suggested that they equilibrated with their corresponding hemiketals, 4 might also be formed from the hemiketals.
23. (a) Nishimura, T.; Uemura, S. Synlett 2004, 201.
24. (b) Satoh, T.; Miura, M. Top. Organomet. Chem. 2005, 14, 1.
25. (c) Murakami, M.; Makino, M.; Ashida, S.; Matsuda, T. Bull. Chem. Soc. Jpn. 2006, 79, 1315.
26. For examples of sequential occurrence of β-hydride elimination and subsequent hydrorhodation on a different unsaturated site, see: (a) Yamabe, H.; Mizuno, A.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2005, 127, 3248.
27. (b) Shintani, R.; Okamoto, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 2872.
28. (c) Martinez, R.; Voica, F.; Genet, J.-P.; Darses, S. Org. Lett. 2007, 9, 3213.
29. For a review, see: Ma, S.; Gu, Z. Angew. Chem., Int. Ed. 2005, 44, 7512.
30. For an excellent example of 1,4-palladium migration from alkyl to aryl followed by carbon-carbon bond formation, see: Huang, Q.; Fazio, A.; Dai, G.; Campo, M. A.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 7460.
31. For reviews on rhodium-catalyzed 1,4-addition, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
32. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
33. For 1,4-addition of organotransition metal species generated in a catalytic way, see: (a) Chang, S.; Na, Y.; Choi, E.; Kim, S. Org. Lett. 2001, 3, 2089.
34. (b) Picquet, M.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1999, 55, 3937.
35. Cyclohex-2-enone, benzaldehyde, and oct-4-yne failed to react with the arylrhodium species.