Asymmetric synthesis of functionalized, monocyclic chlorocyclobutenes

Organic Letters

Volumn 12, Issue 18, 2010, Pages 3994-3997

  Darses, Benjamin ^a   Greene, Andrew E ^a   Poisson, Jean François ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956604815     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101559b     Document Type: Article

References (40)

1. Other than enol and squaric acid derivatives. For some methods of preparation, see
2. Caserio, M. C.; Simmons, H. E., Jr.; Johnson, A. E.; Roberts, J. D. J. Am. Chem. Soc. 1960, 82, 3103-3106
3. Sullivan, R.; Lacher, J. R.; Park, J. D. J. Org. Chem. 1964, 29, 3664-3668
4. Steinmetz, R.; Hartmann, W.; Schenck, G. O. Chem. Ber 1965, 98, 3854-3873
5. Snider, B. B.; Roush, D. M.; Rodini, D. J.; Gonzalez, D.; Spinell, D. J. Org. Chem. 1980, 45, 2773-2785
6. Goodman, M. M.; Shoup, T. PCT Int. Appl. WO 9717092 A1 19970515, 1997.
7. Gourdel-Martin, M.-E.; Huet, F. J. Org. Chem. 1997, 62, 2166-2172
8. Takahashi, T.; Shen, B.; Nakajima, K.; Xi, Z. J. Org. Chem. 1999, 64, 8706-8708
9. Hamura, T.; Kakinuma, M.; Tsuji, S.; Matsumoto, T.; Suzuki, K. Chem. Lett. 2002, 748-749
10. Liu, Y.; Liu, M.; Song, Z. J. Am. Chem. Soc. 2005, 127, 3662-3663
11. Fuörstner, A.; Aiössa, C. J. Am. Chem. Soc. 2006, 128, 6306-6307
12. Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc. 2006, 128, 7430-7431
13. Debleds, O.; Campagne, J.-M. J. Am. Chem. Soc. 2008, 130, 1562-1563
14. Tian, G.-Q.; Yuan, Z.-L.; Zhu, Z.-B.; Shi, M. Chem. Commun. 2008, 2668-2670
15. Xu, H.; Zhang, W.; Shu, D.; Werness, J. B.; Tang, W. Angew. Chem., Int. Ed. 2008, 47, 8933-8936
16. Masarwa, A.; Fuörstner, A.; Marek, I. Chem. Commun. 2009, 5760-5762
17. Barluenga, J.; Riesgo, L.; Lopez, L. A.; Rubio, E.; Tomas, M. Angew. Chem., Int. Ed. 2009, 48, 7569-7572
18. Lopez-Carillo, V.; Echavarren, A. J. Am. Chem. Soc. 2010, 132, 9292-9294
19. For reviews on cyclobutane derivatives, see
20. The Chemistry of Cyclobutanes; Rappoport, Z.; Liebman; J. F., Eds.; John Wiley & Sons, Ltd.: West Sussex, England, 2005; Vols. 1 and 2.
21. Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449-1483
22. For the synthesis of some polycyclic halocyclobutenes, see
23. Hassner, A.; Fletcher, V. R. Tetrahedron Lett. 1970, 58, 5053-5056
24. Ohkita, M.; Ando, K.; Tsuji, T. Chem. Commun. 2001, 2570-2571
25. Fuörstner, A.; Schlecker, A.; Lehmann, C. Chem. Commun. 2007, 4277-4279
26. Allen, A.; Villeneuve, K.; Cockburn, N.; Fatila, E.; Riddell, N.; Tam, W. Eur. J. Org. Chem. 2008, 4178-4192
27. For some routes to enantioenriched cyclobutenes, see
28. Villeneuve, K.; Tam, W. Angew. Chem., Int. Ed. 2004, 43, 610-613
29. Shibata, T.; Takami, K.; Kawachi, A. Org. Lett. 2006, 8, 1343-1345
30. Ishihara, K.; Fushimi, M. J. Am. Chem. Soc. 2008, 130, 7532-7533 and refs 1o, 2b, and 3a
31. Darses, B.; Greene, A. E.; Coote, S. C.; Poisson, J.-F. Org. Lett. 2008, 10, 821-824
32. All enol ethers used in this work were obtained from Stericol [1-(2,4,6-triisopropylphenyl)ethanol] through the dichloroenol and ynol ethers, following a procedure similar to that described in
33. Kann, N.; Bernardes, V.; Greene, A. E. Org. Synth 1997, 74, 13-22 For the mechanism of the formation of ynol ethers from dichloroenol ethers, see:
34. Darses, B.; Milet, A.; Philouze, C.; Greene, A. E.; Poisson, J.-F. Org. Lett. 2008, 10, 4445-4447
35. The relative stereochemistry in 2a has been assigned from considerable antecedent for the face of the cycloaddition and by NOE experiments for the face of the reduction.
36. Reductive elimination was also attempted directly on 2a with chromium perchlorate; however, a mixture of products containing only a minor amount of cyclobutene 4a was produced.
37. For examples of vinylic chloride coupling reactions, see
38. Ramiandrasoa, P.; Bréhon, B.; Thivet, A.; Alami, M.; Cahiez, G. Tetrahedron Lett. 1997, 14, 2447-2450
39. Tan, Z.; Negishi, E. Angew. Chem., Int. Ed. 2006, 45, 762-765
40. Lemay, A. B.; Vulic, K. S.; Ogilvie, W. W. J. Org. Chem. 2006, 71, 3615-3618