Work

C–H Functionalization Approach for the Synthesis of Chiral C 2 -Symmetric 1,5-Cyclooctadiene Ligands

Year: 2019

Type: article

Abstract: Chiral cyclooctadiene (COD) derivatives are readily prepared by rhodium-catalyzed allylic C–H functionalization of COD. Either mono- or difunctionalization of COD is possible generating the products in high yield, diastereoselectivity and enantioselectivity. The double C–H functionalization generates C 2 -symmetric COD derivatives with four new stereogenic centers in >99% ee, which can be readily converted to a series of chiral COD ligands. Preliminary evaluations revealed that the COD ligands can be used in rhodium-catalyzed asymmetric arylation of cyclohex-2-enone, leading to the conjugate addition products in up to 76% ee.

Source: Organic Letters

DOI: 10.1021/acs.orglett.9b03764

Authors: Bowen Zhang, Michael R. Hollerbach, Simon B. Blakey, Huw M. L. Davies

Institution: Emory University

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Center for Selective C-H Functionalization, National Science Foundation, Division of Chemistry