Diastereoselective Synthesis of Vinylcyclopropanes from Dienes and Sulfur Ylides

Abstract

The reaction of aryl- and vinyl-stabilized sulfonium ylides with electron-poor dienes has been investigated. Clean cyclopropanation to 2-aryl- and 2-vinyl-substituted vinylcyclopropanes, with high regio- and stereocontrol, was observed. This new diastereoselective strategy was applied to formal synthesis of lamoxirene and dictyopterene B.

vinylcyclopropane - diene - stereoselective synthesis - sulfur - ylides

References and Notes

For reviews, see:

1a Pietruszka J. Chem. Rev.  2003,  103:  1051 

1b Faust R. Angew. Chem. Int. Ed.  2001,  40:  2251 

1c Sonawane HR. Bellur NS. Kulkarni DG. Ahuja JR. Synlett  1993,  875 

1d The Chemistry of the Cyclopropyl Group   Vol. 1:  Rappoport Z. Wiley and Sons; New York: 1987. 

For some examples, see:

2a Salaün J. Baird MS. Curr. Med. Chem.  1995,  2:  511 

2b Yoshida M. Ezaki M. Hashimoto M. Yamashita M. Shigematsu N. Okuhara M. Kohsaka M. Horikoshi K. J. Antibiotics  1990,  43:  748 

2c Connor DT. Greenough RC. von Strandtmann M. J. Org. Chem.  1977,  42:  3664 

2d Pettus JA. Moore RE. J. Chem. Soc., Chem. Commun.  1970,  17:  1093 

3 For a review, see: Lebel H. Marcoux J.-F. Molinaro C. Charette AB. Chem. Rev.  2003,  103:  977 

For some recent works on the synthesis of vinylcyclopropane carboxylic esters from dienes and diazo compounds, see:

4a Xu Z.-H. Zhu S.-N. Sun X.-L. Tang Y. Dai L.-X. Chem. Commun.  2007,  19:  1960 

4b Adjabeng GM. Gerritsma DA. Bhanabhai H. Frampton CS. Capretta A. Organometallics  2006,  25:  32 

4c Itagaki M. Masumoto K. Yamamoto Y. J. Org. Chem.  2005,  70:  3292 

4d Moreau B. Charette AB. J. Am. Chem. Soc.  2005,  127:  18014 

4e Deng L. Giessert AJ. Gerlitz OO. Dai X. Diver ST. Davies HML. J. Am. Chem. Soc.  2005,  127:  1342 

4f Hahn ND. Nieger M. Dötz KH. Eur. J. Org. Chem.  2004,  1049 

For some recent works on the synthesis of vinylcyclo-propane carboxylic esters from allylic ylides and acrylate derivatives, see:

5a Deng X.-M. Cai P. Ye S. Sun X.-L. Liao W.-W. Li K. Tang Y. Wu Y.-D. Dai L.-X. J. Am. Chem. Soc.  2006,  128:  9730 

5b Kunz RK. MacMillan DWC. J. Am. Chem. Soc.  2005,  127:  3240 

6a Melancon BJ. Perl NR. Taylor RE. Org. Lett.  2007,  9:  1425 

6b He R. Deng M.-Z. Tetrahedron  2002,  58:  7613 

6c Markó IE. Giard T. Sumida S. Gies A.-E. Tetrahedron Lett.  2002,  43:  2317 

6d Luithle JEA. Pietruszka J. J. Org. Chem.  2000,  65:  9194 

6e Zhou S.-M. Yan Y.-L. Deng M.-Z. Synlett  1998,  198 

6f Theberge CR. Verbicky CA. Zercher CK. J. Org. Chem.  1996,  61:  9792 

For punctual examples of one-step methods, see:

7a Deng X.-M. Cai P. Ye S. Sun X.-L. Liao W.-W. Li K. Tang Y. Wu Y.-D. Dai L.-W. J. Am. Chem. Soc.  2006,  128:  9730 

7b Guerreiro MC. Schuchardt U. Synth. Commun.  1996,  26:  1793 

7c Reissig H.-U. Angew. Chem., Int. Ed. Engl.  1996,  35:  971 

8 For the first report on this reaction, see: Corey EJ. Chaykovsky M. J. Am. Chem. Soc.  1965,  87:  1353 

9 For a review, see: Li A.-H. Dai L.-X. Aggarwal VK. Chem. Rev.  1997,  97:  2341 

10a Aggarwal VK. Grange E. Chem. Eur. J.  2006,  12:  568 

10b Ye S. Huang Z.-Z. Xia C.-A. Tang Y. Dai L.-X. J. Am. Chem. Soc.  2002,  124:  2432 

10c Aggarwal VK. Alonso E. Fang GY. Ferrera M. Hynd G. Porcelloni M. Angew. Chem.  2001,  113:  1482 

10d Aggarwal VK. Smith H. Hynd G. Jones RVH. Fieldhouse R. Spey SE. J. Chem. Soc., Perkin Trans. 1  2000,  3267 

10e Solladié-Cavallo A. Diep-Vohuule A. Isarno T. Angew. Chem. Int. Ed.  1998,  37:  1689 

11 Rapoport has shown that reaction of alkyl-substituted sulfonium ylides with diene esters leads preferentially to 1,4-addition. See: Tang CSF. Rapoport H. J. Org. Chem.  1973,  38:  2806 

12 All the salts were readily obtained from tetrahydrothiophene and corresponding substituted benzyl bromides, according to a known procedure. See: Aggarwal VK. Fang GY. Schmidt AT. J. Am. Chem. Soc.  2005,  127:  1642 

13 Patani GA. LaVoie EJ. Chem. Rev.  1996,  96:  3147 

14 Osolapoff GM. J. Am. Chem. Soc.  1948,  70:  1974 

15 Müller DG. Gassmann G. Naturwissenschaften  1980,  67:  462 

16 Hertweck C. Boland W. Tetrahedron  1997,  53:  14651 

17 Boland has also developed an asymmetric synthesis of the cis-isomer of 7 in four steps; see: Hertweck C. Boland W. J. Org. Chem.  2000,  65:  2458 

18a Dorsch D. Kunz E. Helmchen G. Tetrahedron Lett.  1985,  26:  3319 

18b Schotten T. Boland W. Jaenicke L. Helv. Chem. Acta  1985,  68:  1186