Dual-Function Cinchona Alkaloid Catalysis: Catalytic Asymmetric Tandem Conjugate Addition−Protonation for the Direct Creation of Nonadjacent Stereocenters
Citations Over TimeTop 1% of 2006 papers
Abstract
Catalytic tandem asymmetric reactions constitute a powerful strategy for the asymmetric construction of nonadjacent stereocenters in acyclic molecules directly from achiral precursors. In this Communication, we report a highly enantioselective and diastereoselective addition of trisubstituted carbon donors to 2-chloroacrylonitrile catalyzed by bifunctional cinchona alkaloid catalysts. This represents the first asymmetric tandem conjugate addition-protonation with efficient catalytic control of two nonadjacent stereocenters. As demonstrated in a concise and highly stereoselective formal total synthesis of (-)-manzacidin A, this asymmetric tandem reaction establishes a new and versatile catalytic approach for the enantioselective and diastereoselective creation of 1,3-tertiary-quaternary stereocenters.
Related Papers
- → Recent advances in asymmetric organocatalysis mediated by bifunctional amine–thioureas bearing multiple hydrogen-bonding donors(2014)353 cited
- → Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins(2011)170 cited
- → Recent Advances in Natural Products Synthesis Using Bifunctional Organocatalysts Bearing a Hydrogen‐Bonding Donor Moiety(2019)22 cited
- → Enantioselective monofluoromethylation of aldehydes with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide catalyzed by a bifunctional cinchona alkaloid-derived thiourea–titanium complex(2013)30 cited
- → The Organocatalytic α‐Fluorination of Chiral γ‐Nitroaldehydes: the Challenge of Facing the Construction of a Quaternary Fluorinated Stereocenter(2016)17 cited