Related Experiment Video
Updated: May 5, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
General approach to synthesis of chiral branched hydrocarbons in high configurational purity
1U.S. Department of Agriculture, Insect Attractants, Behavior, and Basic Biology Research Laboratory, Agricultural Research Service, 32604, Gainesville, Florida.
Abstract:
Configurationally pure (>99.6%) α-methylalkanoic acids have been employed to prepare chiral hydrocarbon semiochemicals. The stereoisomers of the following compounds were synthesized: 13-methylhentriacontane, 15-methyltritriacontane, and 15,19-dimethyltritriacontane. The first compound was identified earlier as a kairomone of the corn earworm while the other two are sex excitants of the stable fly. The methods described have broad applicability in asymmetric synthesis.
More Related Videos
Related Concept Videos
Prochirality
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Molecules with Multiple Chiral Centers
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Radical Anti-Markovnikov Addition to Alkenes: Overview

