Diverse Alkanones by Catalytic Carbon Insertion into the Formyl C−H Bond. Concise Access to the Natural Precursor of Achyrofuran
作者:Andrew J. Wommack、David C. Moebius、Austin L. Travis、Jason S. Kingsbury
DOI:10.1021/ol9010932
日期:2009.8.6
Over a century ago, the first reactions of diazomethane with aldehydes delivered methyl ketones. In the interim, aldehydes have been homologated with trimethylsilyldiazomethane, diazoacetates, and aryldiazomethanes, on rare occasion with catalysis. This work describes a mild procedure for convergent ketone assembly from nonstabilized diazoalkanes, including examples of chiral ketone synthesis with
Synthesis of Acyclic Ketones by Catalytic, Bidirectional Homologation of Formaldehyde with Nonstabilized Diazoalkanes. Application of a Chiral Diazomethyl(pyrrolidine) in Total Syntheses of Erythroxylon Alkaloids
作者:Andrew J. Wommack、Jason S. Kingsbury
DOI:10.1021/jo401377a
日期:2013.11.1
This work offers a catalytic approach to convergent ketone assembly based upon formal and tandem C–H insertion of diazoalkanes in the presence of limiting amounts of monomeric formaldehyde, which is easily generated as a gas by thermolysis of the inexpensive and abundant paraformaldehyde (∼30 USD/kg). The method forms di-, tri-, and even tetrasubstituted acetones with high efficiency, and it has streamlined