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Asymmetric O–H insertion reaction of carbenoids catalyzed by chiral bicyclo bisoxazoline copper(I) and (II) complexes

Abstract : Chiral copper(I) and (II)-bicyclobisoxazoline complexes were found to catalyze the insertion of α-diazocarbonyl compounds into O–H bonds of alcohols. The insertion reactions of various α-diazopropionates proceeded with moderate yields (40–90%) and high enantioselectivities (up to 92% and 94% with copper(I) and copper(II)-catalysts, respectively). A predominant effect on the enantiocontrol of the reaction was observed when copper(I) and (II)-catalysts were associated with NaBARF and molecular sieves (4 Å). © 2016 Elsevier Ltd
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Submitted on : Friday, November 4, 2016 - 12:20:50 PM
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P. Le Maux, D. Carrié, P. Jéhan, G. Simonneaux. Asymmetric O–H insertion reaction of carbenoids catalyzed by chiral bicyclo bisoxazoline copper(I) and (II) complexes. Tetrahedron, Elsevier, 2016, 72 (31), pp.4671--4675. ⟨10.1016/j.tet.2016.06.044⟩. ⟨hal-01367241⟩

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