Studies Toward Improved Enantiocontrol in the Asymmetric Cu-Catalyzed Reductive Coupling of Ketones and Allenamides: 1,2-Aminoalcohol Synthesis
Stephen F. Collins, Joshua D. Sieber
Abstract
Herein, we report the development of an improved system for the Cu-catalyzed enantioselective reductive coupling of ketones and allenamides through the optimization of the allenamide to avoid an on-cycle rearrangement. High enantioselectivities could be obtained for a variety of ketones. Use of the acyclic allenamides described herein selectively generated anti -diastereomers in contrast to cyclic allenamides that were previously shown to favor the syn -form. A rationale for this change in diastereoselectivity is also presented.
Topics & Concepts
ChemistryDiastereomerEnantioselective synthesisCombinatorial chemistryCatalysisCoupling (piping)Catalytic cycleKetoneOrganic chemistryMechanical engineeringEngineeringCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and Catalysis