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C-2-symmetric fluorous diamines and diimines as ligands for metal-catalysed asymmetric cyclopropanation of styrene

Author(s): I. Shepperson, S. Quici, G. Pozzi, M. Nicoletti, D. O'Hagan

Abstract:
Perfluoroalkyl-substituted, enantiopure C-2-symmetric N and N,O ligands showing affinity either for standard organic solvents or perfluorocarbons have been conveniently prepared from readily available precursors. Preformed cobalt(II) and in-situ-generated copper(I) complexes of these ligands were tested as catalysts in the metal-catalysed cyclopropanation of styrene with diazoacetates. Under optimised reaction conditions, which include the use of a fluorous biphasic system and short reaction times, the copper complex of a C-2-SYM-metric diamine afforded promising results (yield = 77%, trans/cis = 67:33, ee of the trans isomer = 62%) and could be easily separated from the products by simply decanting the fluorous phase. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

Full version: Available here

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ISBN: 1434-193X
Publication Year: 2004
Periodical: European Journal of Organic Chemistry
Periodical Number: 22
Volume:
Pages: 4545-4551
Author Address: