Synthesis of Atropisomers with Biaryl and Vinylaryl Chirality via Pd-Catalyzed Point-to-Axial Chirality Transfer Ring-Opening Reaction
Jian Gu, Biqiong Hong, Xiaoping Xue, Junwei Xi, Zhenhua Gu
Abstract
A palladium-catalyzed domino cyclization/ring-opening reaction between 8H-indeno[1,2-c]thiophen-8-ols and N-(2-bromophenyl)propiolamide derivatives is reported. The reaction features a highly stereospecific point chirality to axial chirality transfer process, which enables the synthesis of molecules containing two chiral axes from the compounds with only one stereogenic center.
Topics & Concepts
StereocenterChirality (physics)ChemistryAtropisomerAxial chiralityRing (chemistry)CatalysisPalladiumStereochemistryMoleculeStereospecificityDominoCombinatorial chemistryEnantioselective synthesisOrganic chemistryPhysicsQuarkNambu–Jona-Lasinio modelQuantum mechanicsChiral symmetry breakingAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityBiological Activity of Diterpenoids and Biflavonoids