Related Experiment Video
Updated: Feb 19, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Synthesis of Chiral (hydro)Indoloquinazolinones via Enantioselective Copper-Catalyzed Borylative Cyclization
Yaqi Zhang1, Wei-Cong Liao1, Tian-Ming Yang1
1School of Chemistry, IGCME, Guangdong Key Lab of Chiral Molecules and Drug Discovery, Sun Yat-sen University, Guangzhou 510006, China.
Abstract:
An asymmetric copper-catalyzed borylative addition protocol enabling the synthesis of a series of chiral (hydro)indoloquinazoline heterocycles with high enantioselectivity (up to 98% ee) and moderate diastereoselectivity is reported here. This catalytic reaction successfully constructs a C2-quaternary stereogenic center within the (hydro)indoloquinazoline framework by employing commercially available diphosphine ligand Xyl-PPhos under mild conditions. The successful scale-up experiments and derivatization studies further demonstrate excellent chiral retention ability.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
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.
Prochirality
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Stereochemical Effects of Enolization
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation