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Allenylidene Induced 1,2‐Metalate Rearrangement of Indole‐Boronates: Diastereoselective Access to Highly Substituted Indolines
Author(s) -
Simlandy Amit Kumar,
Brown M. Kevin
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202103108
Subject(s) - chemistry , indole test , electrophile , catalysis , scope (computer science) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , computer science , programming language
A process to achieve 1,2‐metalate rearrangements of indole boronate as a way to access substituted indolines in high diastereoselectivities is presented. The reaction involves the generation of a Cu–allenylidene, which is sufficiently electrophilic to induce the 1,2‐metalate rearrangement. The scope of the reaction is evaluated as well as further transformations of the product.