Chiral Transient Ligand Enabled Enantioselective Synthesis of Atropisomers Decorated with Unactivated Olefins via a Palladium-Catalyzed C–H Olefination
Vadivel Arjun, Masilamani Jeganmohan
Abstract
Herein, atroposelective synthesis of axially chiral biaryls with unactivated olefins by a palladium-catalyzed C-H olefination using a chiral transient directing group strategy has been disclosed. This protocol is well compatible with a variety of biaryl-2-aldehydes as well as various olefins such as allyl sulfonamides and allyl sulfones to provide the atroposelective olefinated products in synthetically useful yields with excellent enantioselectivities up to >99% ee. In addition, a wide number of axially chiral biaryl alcohols were synthesized by the simple diversification of the products in excellent enantioselectivity.
Topics & Concepts
AtropisomerChemistryEnantioselective synthesisPalladiumCatalysisLigand (biochemistry)Combinatorial chemistryTransient (computer programming)Organic chemistryReceptorBiochemistryComputer scienceOperating systemAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityCatalytic C–H Functionalization Methods