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

ABSTRACT: 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.

SUBMITTER: Ouyang J 

PROVIDER: S-EPMC9121375 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature