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Chelation-Controlled Stereospecific Cross-Coupling Reaction between Alkenes for Atroposelective Synthesis of Axially Chiral Conjugated Dienes

Dong‐Ting Dai, Meng‐Wei Yang, Zhiyuan Chen, Zi‐Lu Wang, Yun‐He Xu

2022Organic Letters37 citationsDOI

Abstract

In this protocol, an efficient palladium-catalyzed asymmetric synthesis of axially chiral conjugated dienes via alkenyl C-H olefination is reported. The corresponding atropisomeric styrenes containing a conjugated diene scaffold were obtained in good yields with good enantioselectivities. This synthetic strategy features an easy operation, mild reaction conditions, a wide functionality tolerance, and high efficiency.

Topics & Concepts

ChemistryConjugated systemStereospecificityCoupling reactionDieneCombinatorial chemistryPalladiumConjugated dieneAxial symmetryCatalysisOrganic chemistryMonomerPolymerEngineeringStructural engineeringNatural rubberAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling
Chelation-Controlled Stereospecific Cross-Coupling Reaction between Alkenes for Atroposelective Synthesis of Axially Chiral Conjugated Dienes | Litcius