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On the Mechanism of the Organocatalytic Asymmetric Epoxidation of α,β‐Unsaturated Aldehydes
Author(s) -
Davis Rebecca L.,
Jensen Kim L.,
Gschwend Björn,
Jørgensen Karl Anker
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303942
Subject(s) - chloral hydrate , catalysis , chemistry , hydrate , organocatalysis , organic chemistry , reaction mechanism , mechanism (biology) , combinatorial chemistry , enantioselective synthesis , philosophy , epistemology , psychology , psychiatry
Mechanistic studies on the organocatalytic epoxidation of α,β‐unsaturated aldehydes explore the autoinductive behavior of the reaction and establish that the hydrate/peroxyhydrate of the product is acting as a phase‐transfer catalyst. Based on these studies, an improved methodology that provides high selectivities and decreased catalyst loading, through the addition of chloral hydrate, is developed.