19771-05-2Relevant academic research and scientific papers
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
Wommack, Andrew J.,Kingsbury, Jason S.
, p. 10573 - 10587 (2013/11/19)
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 a synthesis of (-)-dihydrocuscohygrine in which the absolute stereochemistry of a proline-based starting material is preserved. Assisted by the advent of new protocols for hydrazone oxidation, we also provide full details on handling non-carbonyl-stabilized diazo compounds.
