Journal ArticleDOI
An accelerated diastereoselective variant of the amide acetal Claisen rearrangement
TLDR
Les sels derives de l'alkylation de propionamides ou des fluoroacetamides par le triflate de methyle ou le sulfate de dimethyle reagissent avec un alcoolate de Li derive du cis- ou trans-butene-2ol-1 pour donner directement le produit de transposition sigmatrope 3,3 des N,O-ceteneacetals correspondants.Abstract:
Les sels derives de l'alkylation de propionamides ou des fluoroacetamides par le triflate de methyle ou le sulfate de dimethyle reagissent avec un alcoolate de Li derive du cis- ou trans-butene-2ol-1 pour donner directement le produit de transposition sigmatrope 3,3 des N,O-ceteneacetals correspondantsread more
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Book ChapterDOI
7.2 – Claisen Rearrangements
TL;DR: In this paper, a survey of variants of the Claisen rearrangement that are of general use in stereoselective organic synthesis is presented, highlighting the influence of steric and electronic parameters on transition state geometries.
Journal ArticleDOI
Theory of Substituent Effects on Pericyclic Reaction Rates: Alkoxy Substituents in the Claisen Rearrangement
Hi Young Yoo,K. N. Houk +1 more
TL;DR: In this article, transition structures, activation energies, and reaction energies were calculated by ab initio quantum mechanical methods for the Claisen rearrangements of five hydroxy-substituted allyl vinyl ethers.
Journal ArticleDOI
The enantioselective fluoroacetamide acetal claisen rearrangements of N-fluoroacetyl-trans-(2R,5R)-2,5-dimethylpyrrolidine
TL;DR: In this paper, it was shown that the chiral auxiliary directed the approach of the crotyl fragment to the Si face of the (E )-N,O -ketene acetal.
Journal ArticleDOI
Dual Nucleophilic/Electrophilic Capture of In Situ Generated Iminium Ethers: Towards the Synthesis of Functionalized Amide Building Blocks
TL;DR: The method takes advantage of a novel Claisen rearrangement and the use of aromatic substrates greatly facilitates the formation of the intermediate iminium ether.