Work

Design of an Organocatalytic Asymmetric (4 + 3) Cycloaddition of 2-Indolylalcohols with Dienolsilanes

Year: 2022

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Here we present the design of a highly enantioselective, catalytic (4 + 3) cycloaddition of gem -dialkyl 2-indolyl alcohols and dienolsilanes, enabled by strong and confined IDPi Lewis acids. The method furnishes novel bicyclo[3.2.2]cyclohepta[ b ]indoles with up to three stereogenic centers, one of which is quaternary. A broad substrate scope is accompanied by versatile downstream chemical modifications. Density functional theory-supported mechanistic studies shed light on the importance of the in situ generated silylium species in an overall concerted yet asynchronous cycloaddition.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.2c02216

Authors: Jie Ouyang, Rajat Maji, Markus Leutzsch, Benjamin Mitschke, Benjamin List

Institutions: Max-Planck-Institut für Kohlenforschung, Hokkaido University, Institute for Chemical Reaction Design and Discovery

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: Verband der Chemischen Industrie, Deutsche Forschungsgemeinschaft, H2020 European Research Council, H2020 Marie Skłodowska-Curie Actions