We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
A Cooperative Hydrogen Bond Donor–Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.
- Authors
Maskeri, Mark A.; O'Connor, Matthew J.; Jaworski, Ashley A.; Davies, Anna V.; Scheidt, Karl A.
- Abstract
Carbocations stabilized by adjacent oxygen atoms are useful reactive intermediates involved in fundamental chemical transformations. These oxocarbenium ions typically lack sufficient electron density to engage established chiral Brønsted or Lewis acid catalysts, presenting a major challenge to their widespread application in asymmetric catalysis. Leading methods for selectivity operate primarily through electrostatic pairing between the oxocarbenium ion and a chiral counterion. A general approach to new enantioselective transformations of oxocarbenium ions requires novel strategies that address the weak binding capabilities of these intermediates. We demonstrate herein a novel cooperative catalysis system for selective reactions with oxocarbenium ions. This new strategy has been applied to a highly selective and rapid oxa‐Pictet–Spengler reaction and highlights a powerful combination of an achiral hydrogen bond donor with a chiral Brønsted acid.
- Subjects
HYDROGEN bonding; BRONSTED acids; ENANTIOSELECTIVE catalysis; TETRAHYDROPYRANYL compounds; CHEMICAL reactions
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 52, p17471
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201811383