Solvent Effects and Mechanistic Studies for Re 2 O 7 -Catalyzed Allylative Annulation Reactions

The sequence of allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition results in the formation of a ring while serving as a fragment-coupling and stereocenter-generating reaction. Successful applications of these processes require a balancing o...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2022-02, Vol.87 (3), p.1830-1839
Main Authors: Anderson, Shelby M, Van Engen, Marcus D, Floreancig, Paul E
Format: Article
Language:English
Subjects:
Catalysis
Solvents
Stereoisomerism
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The sequence of allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition results in the formation of a ring while serving as a fragment-coupling and stereocenter-generating reaction. Successful applications of these processes require a balancing of the kinetics of numerous productive and unproductive steps. This work describes the manner in which solvent changes can be used to expand the scope and change the stereochemical outcomes of these processes. Mechanistic studies provide greater insight into the nuances of the transformations and the reactive species that are generated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02466