Litcius/Paper detail

Catalytic Asymmetric Iodoesterification of Simple Alkenes

Takayoshi Arai, Kodai Horigane, Takumi Suzuki, Ryosuke Itoh, Masahiro Yamanaka

2020Angewandte Chemie International Edition25 citationsDOI

Abstract

Abstract Catalytic asymmetric iodoesterification of simple alkenes was achieved using a dinuclear zinc‐3,3′‐( R , S , S )‐bis(aminoimino)binaphthoxide ( di‐Zn ) complex. For iodoesterification using p ‐methoxybenzoic acid, the N ‐iodonaphthalenimide (NIN)‐I 2 system was effective for producing iodoesters in a highly enantioselective manner. The synthetic utility of chiral iodo‐ p ‐methoxybenzoates was also demonstrated. The quartet of metal ionic bond, hydrogen bond, halogen bond, and π‐π stacking is harmonized on the single reaction sphere of di‐Zn catalyst for enabling the highly enantioselective catalytic asymmetric iodoesterification of simple alkenes for the first time.

Topics & Concepts

Simple (philosophy)CatalysisChemistryOrganic chemistryPhilosophyEpistemologyVanadium and Halogenation ChemistryOxidative Organic Chemistry ReactionsChemical Synthesis and Reactions