title: Exploration of the enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters.
abstract: Quaternary stereocenters on a 2-cyclohexen-1-one ring are synthesized with good to excellent levels of enantioselectivity. The quaternary stereocenter is created through a new synthetic sequence involving three reactions: the enantioselective Birch reduction-allylation, enol ether hydrolysis, and the Cope rearrangement. To illustrate the ability of the sequence to enantioselectively generate complex structures, a variety of substrates are described. Notably, the sequence works for the enantioselective generation of vicinal quaternary-tertiary stereocenters, the generation of congested arylic quaternary stereocenters, and hydroxyalkyl substituted quaternary stereocenters.
authors.affiliation: Department of Chemistry, Bryn Mawr College, Bryn Mawr, Pennsylvania 19010-2899, USA.
authors.forename: Tapas
authors.initials: T
authors.lastname: Paul
authors.forename: William P
authors.initials: WP
authors.lastname: Malachowski
authors.forename: Jisun
authors.initials: J
authors.lastname: Lee
mesh_terms: D003512:Cyclohexanones / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis*; D006900:Hydroxylation; D008956:Models, Chemical; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones; D053138:Cyclohexenes; D006844:Hydrocarbons, Cyclic