Recovery of carbonyl compounds from N,N-dialkylhydrazones.
Deprotonation of enantiomerically pure hydrazones and subsequent trapping with suitable electrophiles generates new stereogenic centers with excellent stereoselectivity. To liberate the original carbonyl functionality in the final products, it is necessary to cleave the hydrazone moiety. In recent years, many reagents have been developed to regenerate carbonyl compounds from the corresponding dialkylhydrazones which are compatible with a wide range of functionalities. This has allowed the use of hydrazones in the total synthesis of complex natural products. This Account is meant to be an overview of methods which are classified as oxidative, hydrolytic, and reductive cleavage procedures.
Enders
D
D
Institut für Organische Chemie der Technischen Hochschule, Professor-Pirlet-Strasse 1, D-52074 Aachen, Germany. Enders@RWTH_Aachen.de
Wortmann
L
L
Peters
R
R
D006835:Hydrazones / Q000737:chemistry*; D006868:Hydrolysis; D010084:Oxidation-Reduction
D006835:Hydrazones