An Expedient and Practical Method for the Synthesis of a Diverse Series of Cyclopropane α-Amino Acids and Amines

Citations Over TimeTop 10% of 2004 papers

Abstract

A practical synthesis for the preparation of a diverse series of cyclopropane alpha-amino acids is described. Nitrocyclopropane carboxylates can be readily prepared through treatment of alpha-nitroesters and iodobenzene diacetate or alpha-nitro-alpha-diazoesters with a Rh(II) catalyst and an olefin. Reduction of the nitro group using zinc/HCl in i-PrOH affords substituted cyclopropane alpha-amino esters in modest to high yields (54-99%). A "one-pot" procedure involving sequential cyclopropanation and reduction is described. The method can also be applied to the preparation of arylcyclopropyl amines (three examples).

Related Papers

• → trans-Directing Ability of the Amide Group: Enabling the Enantiocontrol in the Synthesis of 1,1-Dicarboxy Cyclopropanes. Reaction Development, Scope, and Synthetic Applications(2009)76 cited
• → PIII-Mediated intramolecular cyclopropanation and metal-free synthesis of cyclopropane-fused heterocycles(2020)34 cited
• → Preparation of Optically Active cis-Cyclopropane Carboxylates: Cyclopropanation of α-Silyl Stryenes with Aryldiazoacetates and Desilylation of the Resulting Silyl Cyclopropanes(2016)28 cited
• → Wadsworth Emmons cyclopropanation mediated diastereoselective Syntheses of α-epoxy- trans-disubstituted cyclopropane and α-hydroxy-trans-disubstituted cyclopropane(2021)8 cited
• → Direct synthesis of per(poly)fluoroalkylmethyl‐substituted electrophilic cyclopropane derivatives(1995)2 cited