The Journal of organic chemistry

Synthesis of Acyclic Ketones by Catalytic, Bidirectional Homologation of Formaldehyde with Nonstabilized Diazoalkanes. Application of a Chiral Diazomethyl ( …

AJ Wommack, JS Kingsbury

Index: Wommack, Andrew J.; Kingsbury, Jason S. Journal of Organic Chemistry, 2013 , vol. 78, # 21 p. 10573 - 10587

Full Text: HTML

Citation Number: 15

Abstract

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 (−)- ...