First intermolecular cyclopropanation of Fischer dialkylaminocarbene complexes. Synthesis of 1-aminocyclopropanecarboxylic acid derivatives.
[reaction: see text] The first cyclopropanation reaction of olefins with Fischer dialkylaminocarbene complexes is presented. The reaction yields 1-aminocyclopropanecarboxylic acid derivatives in a single step, usually with high diastereoselectivity. An approach to the asymmetric version of this reaction is also presented. The synthetic utility of the procedure is exemplified by the synthesis of both cycles of metanoproline in a single step. In addition, the synthesis of the first Fischer carbene containing a halocarbonyl group is reported.
Barluenga
José
J
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería 8, E-33701 Oviedo, Spain. barluenga@sauron.quimica.uniovi.es
Aznar
Fernando
F
Gutiérrez
Ignacio
I
García-Granda
Santiago
S
Llorca-Baragaño
M Amparo
MA