Ln(OTf)3-Catalyzed Insertion of Aryl Isocyanides into the Cyclopropane Ring

Vadim S. Korotkov; Oleg V. Larionov; Armin de Meijere

doi:10.1055/s-2006-942514

PAPER

Ln(OTf)₃-Catalyzed Insertion of Aryl Isocyanides into the Cyclopropane Ring [1]

Vadim S. Korotkov, Oleg V. Larionov, Armin de Meijere*
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Fax: +49(551)399475; e-Mail: Armin.deMeijere@chemie.uni-goettingen.de;

Abstract

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Abstract

The insertion of two molecules of an aryl isocyanide into bisacceptor-activated cyclopropane derivatives has been observed for the first time. The reaction proceeds best under the catalysis of Pr(OTf)₃ and offers a facile access to the synthetically useful and potentially pharmacologically relevant substituted dialkyl 3-(arylamino)-2-(arylimino)cyclopent-3-ene-1,1-dicarboxylates in moderate yields (21-65%).

Key words

catalysis - cycloadditions - imines - lanthanides - Lewis acids

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References

Part 128 in the series: Cyclopropyl Building Blocks for Organic Synthesis.

1a

For part 127, see: Tanguy, C.; Bertus, P.; Szymoniak, J.; Larionov, O. V.; de Meijere, A. Synlett 2006, in press.

1b For part 125, see: Larionov O. V. de Meijere A. Adv. Synth. Catal. 2006, 348: 1071-1078

2a de Meijere A. Angew. Chem., Int. Ed. Engl. 1979, 18: 809 ; Angew. Chem. 1979, 91, 867

2b Wiberg KB. In Houben-Weyl, Methods of Organic Chemistry Vol. E17a: de Meijere A. Thieme; Stuttgart: 1997. p.1ff

3 Houben-Weyl, Methods of Organic Chemistry Vol. E17: de Meijere A. Thieme; Stuttgart: 1997.

4a Yu M. Pagenkopf BL. Tetrahedron 2005, 61: 321

4b Reissig H.-U. Zimmer R. Chem. Rev. 2003, 103: 1151

4c Wong HNC. Hon M.-Y. Tse C.-W. Yip Y.-C. Tanko J. Hudlicky T. Chem. Rev. 1989, 89: 165

4d Danishefsky S. Acc. Chem. Res. 1979, 12: 66

5a Pohlhaus PD. Johnson JS. J. Am. Chem. Soc. 2005, 127: 16014

5b Pohlhaus PD. Johnson JS. J. Org. Chem. 2005, 70: 1057

5c Min S. Yang Y.-H. Bo X. Tetrahedron 2005, 61: 1893

5d Bernard AM. Frongia A. Piras PP. Secci F. Spiga M. Org. Lett. 2005, 7: 4565

5e Fuchibe K. Aoki Y. Akiyama T. Chem. Lett. 2005, 34: 538

6a Carson CA. Kerr MA. J. Org. Chem. 2005, 70: 8242

6b Wurz RP. Charette AB. Org. Lett. 2005, 7: 2313

7a Cardona F. Goti A. Angew. Chem. Int. Ed. 2005, 44: 7832 ; Angew. Chem. 2005, 117, 8042

7b Sibi MP. Ma ZH. Jasperse CP. J. Am. Chem. Soc. 2005, 127: 5764

7c Ganton MD. Kerr MA. J. Org. Chem. 2004, 69: 8554

7d Young IS. Kerr MA. Angew. Chem. Int. Ed. 2003, 42: 3023 ; Angew. Chem. 2003, 115, 3131

8a Yadav VK. Sriramurthy V. Org. Lett. 2004, 6: 4495

8b Yadav VK. Sriramurthy V. Angew. Chem. Int. Ed. 2004, 43: 2669 ; Angew. Chem. 2004, 116, 2723

9a Yu M. Pagenkopf BL. Org. Lett. 2001, 3: 2563

9b Yu M. Lynch V. Pagenkopf BL. J. Am. Chem. Soc. 2003, 125: 8122

9c Yu M. Pagenkopf BL. Org. Lett. 2003, 5: 5099

10 Oshita M. Yamashita K. Tobisu M. Chatani N. J. Am. Chem. Soc. 2005, 127: 761

11 Bez G. Zhao C.-G. Org. Lett. 2003, 5: 4991

12 Yoshioka S. Oshita M. Tobisu M. Chantani N. Org. Lett. 2005, 7: 3697

13 Larionov OV. de Meijere A. Angew. Chem. Int. Ed. 2005, 44: 5664 ; Angew. Chem. 2005, 117, 5809

14 See for example: Binotti B. Carfagna C. Zuccaccia C. Macchioni A. Chem. Commun. 2005, 92

Ln(OTf)3-Catalyzed Insertion of Aryl Isocyanides into the Cyclopropane Ring [1]

Ln(OTf)₃-Catalyzed Insertion of Aryl Isocyanides into the Cyclopropane Ring [1]