Related Experiment Video
Updated: Sep 20, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Ni-Catalyzed Enantioselective Dialkyl Carbinol Synthesis via Decarboxylative Cross-Coupling: Development, Scope, and
Yang Gao1, Benxiang Zhang1, Laura Levy1
1Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Abstract:
The first enantioselective decarboxylative Negishi-type alkylations of α-oxy carboxylic acids are reported via the intermediacy of redox-active esters (RAEs). This transformation enables a radical-based retrosynthesis of seemingly trivial enantiopure dialkyl carbinols. This article includes a discussion of the history of such couplings, the retrosynthetic ramifications of such a coupling, the development of general conditions, and an extensive series of applications that vividly demonstrate how it can simplify synthesis.
More Related Videos
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
06:31Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
Published on: November 27, 2015
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Cycloaddition Reactions: Overview
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...