Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor-Acceptor Cyclopropanes and Alkyl Halides

Saikat Das; Constantin G Daniliuc; Armido Studer

doi:10.1002/anie.201711923

Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor-Acceptor Cyclopropanes and Alkyl Halides

Angew Chem Int Ed Engl. 2018 Apr 3;57(15):4053-4057. doi: 10.1002/anie.201711923. Epub 2018 Mar 9.

Authors

Saikat Das¹, Constantin G Daniliuc¹, Armido Studer¹

Affiliation

¹ NRW Graduate School of Chemistry, Organisch-Chemisches Institut, Westfälische Wilhelms-Universität, Corrensstrasse 40, 48149, Münster, Germany.

PMID: 29453816
DOI: 10.1002/anie.201711923

Abstract

Indolylboron ate complexes readily generated from 2-lithioindoles and boronic esters underwent multicomponent dearomative coupling with D-A cyclopropanes and alkyl halides in the presence of Sc(OTf)₃ as a catalyst. The reactions proceeded with complete diastereoselectivity and excellent stereospecificity to provide indolines containing three contiguous stereocenters. The valuable boronic ester moiety remains in the product and allows for subsequent functionalization.

Keywords: boron; donor-acceptor cyclopropanes; multicomponent reactions; ring-opening reactions; stereospecificity.

Publication types

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