One-Step Ruthenium-Catalysed Transformation of 1,7-Enynes into Strained Bicyclic Amino Esters

S. Moulin (1) , T. Roisnel (1) , S. Dérien (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

The reaction of 1,7-enynes, synthesised from α-amino acids, carried out with diazo compounds in the presence of the Cp*RuCl(cod) catalyst allowed the one-step preparation of various strained bicyclic pipecolic acid derivatives in good yields under mild conditions. The stereoselectivity of the created double bond depends on the nature of the diazoalkane, and the diastereoselectivity arises essentially from steric factors. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Domains: Chemical Sciences

S. Moulin, T. Roisnel, S. Dérien. One-Step Ruthenium-Catalysed Transformation of 1,7-Enynes into Strained Bicyclic Amino Esters. European Journal of Organic Chemistry, 2016, 2016 (25), pp.4311--4314. ⟨10.1002/ejoc.201600896⟩. ⟨hal-01367239⟩