Palladium(0) Catalyzed Tandem Alkylation and SN' Cyclization of 1,4-Dichlorobut-2-ene. A One Pot Stereoselective Synthesis of Highly Functionalized Cyclopropanes

Synlett

Volumn 1996, Issue 11, 1996, Pages 1067-1070

  Franzone, Gianluca ^a   Carle, Stéphanie ^a   Dorizon, Philippe ^a   Ollivier, Jean ^a   Salaün, Jacques ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542499953     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5661     Document Type: Article

References (26)

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2. (b) Salaün, J. Top. Curr. Chem., Springer-Verlag Berlin, 1988, Vol. 144, pp. 1-71 ;
3. (c) Schnaubelt, J.; Ullmann, A.; Reissig, H.-U. Synlett 1995, 1223-1225.
4. For a review, see : Salaün, J.; Baird, M.S. Curr. Med. Chem. 1995, 2, pp 511-542, and references cited therein.
5. Gaucher, A.; Dorizon, Ph.; Ollivier, J.; Salaün, J. Tetrahedron Lett. 1995, 36, 2979-2982.
6. For asymmetric syntheses of ACCs, see : Gaucher, A.; Ollivier, J.; Marguerite, J.; Paugam, R.; Salaün, J. Can. J. Chem. 1994, 72, 1312-1327; Dorizon, Ph.; Ollivier, J.; Salaün, J. Synlett, 1996, 1071.
7. For asymmetric syntheses of ACCs, see : Gaucher, A.; Ollivier, J.; Marguerite, J.; Paugam, R.; Salaün, J. Can. J. Chem. 1994, 72, 1312-1327; Dorizon, Ph.; Ollivier, J.; Salaün, J. Synlett, 1996, 1071.
8. Molecular mechanic calculations have been performed with the MAD (Molecular Advanced Design) version 2.3, using a MM2 type force field modified following Norrby suggestion (Norrby, P.O.; Akermark, B.; Hoeffner, F.; Hansson, S.; Blomberg, M. J. Am. Chem. Soc., 1993, 115, 4869), available from Oxford Molecular, Ecole Polytechnique, Palaiseau (France).
9. Bäckvall, J.E.; Vågberg, J.O.; Zercher, C.; Genêt, J.P.; Denis, A. J. Org. Chem. 1987, 52, 5430-5435.
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16. +, 0.6), 150 (3.6, M-15), 123 (7.2), 95 (3), 84 (17.4), 74 (9.2), 73 (100), 43 (11.4).
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19. Tamao, K.; Nakajima, T.; Sumiya, R.; Arai, H.; Higuchi, N.; Ito, Y. Organometallics 1983, 2, 1694-1996; Hale, R.M.; Hoveyda, A.H. J. Org. Chem. 1994, 59, 4370-4374 ; Knölker, H.J.; Wanzl, G. Synlett 1995, 378-382.
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26. For the asymmetric synthesis of such cyclopropanecarbonitriles, see Dorizon, P.; Ollivier, J.; Salaün, J. Synlett 1996, 1071.