Premium
Synthesis of Indanones and Spiroindanones by Diastereoselective Annulation Based on a Hydrogen Autotransfer Strategy
Author(s) -
Chen Yate,
Ding Zhengtian,
Wang Yiming,
Liu Wenfeng,
Kong Wangqing
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202013792
Subject(s) - chemistry , annulation , pyrrolidine , combinatorial chemistry , catalysis , domino , functional group , substrate (aquarium) , reaction conditions , organic chemistry , oceanography , geology , polymer
An unprecedented nickel‐catalyzed domino reductive cyclization of alkynes and o ‐bromoaryl aldehydes is described. The reaction features broad substrate scope and is tolerant of a variety of functional groups, providing straightforward access to biologically significant indanones and spiroindanone pyrrolidine derivatives in good yields with excellent regio‐ and diastereoselectivity. Preliminary mechanistic studies have shown that indanones are formed by the cyclization of o ‐bromoaryl aldehydes and alkynes to form indenol intermediates, followed by hydrogen autotransfer.