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This is in contrast to the behavior of (methylenecyclopropane)copper intermediates which undergo coupling with the electrophilic glycine equivalent only with concomitant opening of a cyclopropane ring. cf. S. I. Kozhushkov. M. Brandl, D. S. Yufit, R. Machinek, A. de Meijere, Liebigs Ann. 1997, 2197-2204.
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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 IEZ, UK [Fax: (internat.) + (1223)336-033, E-mail: teched@chemcrys.cam.ac.uk]. The deposition numbers are CCDC 118933 (14-Me), CCDC 118932 (14-Bn) and CCDC 118954 (34).
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61
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note
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The isomers A and B did not react at all, neither with zinc-copper couple to remove the chlorine atom, nor with sodium azide to form a substitution product. The isomers C and D yielded a single diastereomer in the reductive dehalogenation which means that they should be enantiomers with respect to the stereogenic center C-2.
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