RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2008(4): 517-520
DOI: 10.1055/s-2008-1032080
DOI: 10.1055/s-2008-1032080
LETTER
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Synthesis of Vinylcyclopropanes from Dienes and Sulfur Ylides
Weitere Informationen
Received
16 November 2007
Publikationsdatum:
12. Februar 2008 (online)
Publikationsverlauf
Publikationsdatum:
12. Februar 2008 (online)
![](https://www.thieme-connect.de/media/synlett/200804/lookinside/thumbnails/10.1055-s-2008-1032080-1.jpg)
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.
Key words
vinylcyclopropane - diene - stereoselective synthesis - sulfur - ylides
- 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