An endo-Directing-Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes

Olga O Sokolova; John F Bower

doi:10.1002/anie.202205007

An endo-Directing-Group Strategy Unlocks Enantioselective (3+1+2) Carbonylative Cycloadditions of Aminocyclopropanes

Angew Chem Int Ed Engl. 2022 Aug 8;61(32):e202205007. doi: 10.1002/anie.202205007. Epub 2022 Jun 24.

Authors

Olga O Sokolova¹, John F Bower²

Affiliations

¹ School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.
² Department of Chemistry, University of Liverpool, Crown Street, Liverpool, L69 7ZD, UK.

Abstract

An endo-directing group strategy enables enantioselective (3+1+2) cycloadditions that are triggered by carbonylative C-C bond activation of cyclopropanes. These processes are rare examples of cycloadditions where C-C bond oxidative addition is enantiodetermining, and the first where this is achieved within the context of a multicomponent (higher order) reaction design.

Keywords: Cycloaddition; Cyclopropanes; Enantioselectivity; Rhodium; Synthetic Methods.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cycloaddition Reaction
Cyclopropanes* / chemistry
Stereoisomerism

Substances

Cyclopropanes

Grants and funding

639594/ERC_/European Research Council/International