Substrate versus catalyst control of stereoselectivity in the cyclopropanation of a carbon-carbon double bond linked to the reactant diazoacetate through a chiral linker

Advanced Synthesis and Catalysis

Volumn 348, Issue 4-5, 2006, Pages 449-455

  Weathers Jr , Thomas M ^a   Doyle, Michael P ^a   Carducci, Michael D ^b  

^a Bldg 142   (United States)

^b University of Arizona   (United States)

Author keywords

Addition; Carboxamidates; Configurational bias; Copper(I); Diastereoselectivity; Dirhodium(II); Macrocyclization

Indexed keywords

EID: 33645935669     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200505357     Document Type: Article

References (29)

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13. [5a] and M. P. Doyle, W. R. Winchester, J. A. A. Hoorn, V. Lynch, S. H. Simonsen, R. Ghosh, J. Am. Chem. Soc. 1993, 115, 9968;
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15. 2 symmetry of the bis-oxazoline ligand, see Chapter 4 of ref.[1b]
16. Ligands are arranged so that there are two nitrogens and two oxygens on each rhodium and that the two nitrogens (or two oxygens) are cis to each other: M. P. Doyle, T. Ren, in Progress in Inorganic Chemistry, (Ed.: K. Karlin), Wiley, New York, 2001, Vol. 49, pp 113-168.
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19. Cyclopropane geometry was assigned based on the J-coupling values of the signals correlating to the cyclopropane protons of 12a and 12b (dt, J=5.1, 8.2 Hz and dt, J=5.2, 8.0 Hz).
20. -3.
21. Several of these reactions were repeated, including that of dirhodium(II) tetraacetate and 8. The resulting product ratios obtained from GC analysis in these reactions showed that the peak area ratios varied by 1-3% in three runs of the same reaction.
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26. M. P. Doyle, A. B. Dyatkin, M. N. Protopopova, C. I. Yang, C. S. Miertschin, W. R. Winchester, S. I. Simonsen, V. Lynch, R. Ghosh, Recueil Trav. Chim. Pays-Bas, 1995, 114, 163.
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28. H. M. L. Davies, P. R. Bruzinski, D. H. Lake, N. Kong, M. J. Fall, J. Am. Chem. Soc. 1996, 118, 6897.
29. 1H NMR spectrum shows that the olefinic protons of the allyl ether have not changed in chemical shift or J-coupling values. In addition, the signals for each methyl group of the starting diazoacetate 8 are present in the spectrum. No signals consistent with maleate or fumarate esters (singlet at 6.9 or 6.3 ppm) are observed.