Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.

ABSTRACT: A highly regio- and diastereoselective nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl ketones and cyclopropyl carbinol derivatives using TMSBr, DMPSCl and TMSN₃ as nucleophiles has been developed. A variety of acyclic tertiary alkyl bromides, chlorides and azides were therefore prepared with excellent diastereopurity. The substitution occurs at the most substituted quaternary carbon center in a stereoinvertive manner, which may be attributed to the existence of a bicyclobutonium species.

SUBMITTER: Chen X 

PROVIDER: S-EPMC9324837 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature