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For a recent comprehensive review of the literature, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998; Chapter 4, pp 183-203.
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Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin; Chapter 16
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(b) Doyle M. P.; McKervey, M. A.; Ye, T. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Chapter 16, pp. 513-603.
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(a) Maxwell, J. L.; O'Malley, S.; Brown, K. C.; Kodadek, T. Organometallics 1992, 11, 645.
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Maxwell, J.L.1
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(b) Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron 2000, 56, 3501.
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(c) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647.
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(b) Stoop, R. M.; Bachmann, S.; Valentini, M.; Mezzetti, A. Organometallics 2000, 19, 4117.
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(a) Shen, J. Y.; Slugovc, C.; Wiede, P.; Mereiter, K.; Schmid, R.; Kirchner, K. Inorg. Chim. Acta 1998, 268, 69.
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(b) Costella, L.; Del Zotto, A.; Mezzetti, A.; Zangrando, E.; Rigo, P. J. Chem. Soc., Dalton Trans. 1993, 3001.
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Gao, J. X.; Ikariya, T.; Noyori, R. Organometallics 1996, 15, 1087.
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Gao, J.X.1
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25
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0011483970
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note
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No reaction is observed at room temperature in the presence of 2b. A slight catalytic activity can be observed with the dichloro derivative 2b in dichloroethane at reflux (43% conversion, 3% yield. 86:14 cis-to-trans ratio), but 1 and 2 are formed with low enantioselectivity (4 and 2% ee, respectively), suggesting that the largest contribution to the reaction is due to the uncatalyzed (thermic) reaction.
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26
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0011484736
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note
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GC analysis of the coupling products is inadeuate, as ethyl diazoacetate dimerizes to fumarate and maleate during the chromatographic analysis.
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27
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0011436496
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note
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Decomposition products of 3, or the uncatalyzed thermal decomposition of the diazoester, can be responsible for the formation of 6 and 7 during cyclopropanation.
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29
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0033855933
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(b) Del Zotto, A.; Baratta, W.; Verardo, G.; Rigo, P. Eur. J. Org. Chem. 2000, 2795.
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Eur. J. Org. Chem.
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Del Zotto, A.1
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Rigo, P.4
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31
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0028080271
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note
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(b) Kanemasa, S.; Hamura, S.; Harada, E.; Yamamoto, H. Tetrahedron Lett. 1994, 35, 7985. See also ref 1.
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Tetrahedron Lett.
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Kanemasa, S.1
Hamura, S.2
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Yamamoto, H.4
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32
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0000581242
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Doyle, M. P.; Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Gosh, R. J. Am. Chem. Soc. 1993, 115, 9968.
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Schwab, P.; France, M. B.; Ziller, J. W,; Grubbs, R. H. Angew. Chem. 1995, 107, 2179.
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34
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0011392642
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note
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In contrast, the reaction of 3b with ethyl adiazoacetate at -50°C gives two different carbene complexes 11b′ and 11b″. In both complexes the carbene ligand is cis to both phosphines, as indicated by the P,C(carbene) coupling constants (see Experimental Part). Thus, we assume that these species are the two cis-β isomers featuring a trans C-Ru-N arrangement.
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36
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0042041206
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Cerius2 uses the Universal Force Field (UFF): Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
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Rappé, A.K.1
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Colwell, K.S.3
Goddard W.A. III4
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37
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4243992753
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Rappé, A. K.; Colwell, K. S.; Casewit, C. J. Inorg. Chem. 1993, 32, 3438.
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38
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0033518572
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note
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2: Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
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Hoveyda, A.H.4
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39
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0011393194
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note
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In a MM study of the rhodium(II) carbamidato system, Doyle has reported similar considerations.
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40
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0011446727
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note
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The only exception to this general assumption we are aware of has been suggested by Kodadek to explain the cis selectivity observed with rhodium porphyrins. According to his model, the olefin attacks the carbene with the C=C double bond perpendicular to the M-C vector and parallel to the plane of the porphyrin. However, the olefin rotates before reaching the transition state, and the side-on approach also leads to an end-on transition state in which both double bonds are parallel.
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41
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0000979922
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(a) Song, J. H.; Cho, D. J.; Jeon, S. J.; Kim, Y. H.; Kim, T. J.; Jeong, H. H. Inorg. Chem. 1999, 38, 893.
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(c) Lee, H. M.; Bianchini, C.; Jia, G.; Barbaro, P. Organometallics 1999, 18, 1961.
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0000148948
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(d) Stoop, R. M.; Bauer, C.; Setz, P.; Wörle, M.; Wong, T. Y. H.; Mezzetti, A. Organometallics 1999, 18, 5691.
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0034226418
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