Related Experiment Video
Updated: Jul 18, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular alpha-arylation
Takafumi Arao1, Kazuhiro Kondo, Toyohiko Aoyama
1Graduate School of Pharmaceutical Sciences, Nagoya City University.
Abstract:
The catalyst comprised of Pd(OAc)(2) and H(8)-BINAP provides good reaction conversions for a catalytic enantioselective intramolecular alpha-arylation of N-(2-bromophenyl)-N-methyl-2-arylpropanamide to form the quaternary carbon with up to 68% enantioselectivity.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
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 stereochemistry.
Radicals: Electronic Structure and Geometry
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:

