Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization

C Olier, M Kaafarani, S Gastaldi, MP Bertrand - Tetrahedron, 2010 - Elsevier
The Prins reaction 1 is often related to the Kriewitz reaction. 2 The latter leads to unsaturated
alcohol 1 from a-pinene and formaldehyde through a thermal 'ene-rearrangement'(Eq. 1) …

The Prins reaction: Advances and applications

IM Pastor, M Yus - Current Organic Chemistry, 2007 - ingentaconnect.com
The acid-catalyzed alkene-aldehyde condensation, known as the Prins reaction, is
reviewed. Lewis acids, organic acids and supported catalysts have been reported to assist …

Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst

C Moreau, A Finiels, L Vanoye - Journal of Molecular Catalysis A: Chemical, 2006 - Elsevier
The acid-catalyzed dehydration of fructose was performed in a microbatch reactor at 90° C
using 1-H-3-methyl imidazolium chloride, HMIM+ Cl−, acting both as solvent and catalyst. A …

<? ACS-CT-START-Insert?> Update 1 of:<? ACS-CT-END-Insert?> Ionic Liquids in Heterocyclic Synthesis

MAP Martins, CP Frizzo… - Chemical …, 2014 - ACS Publications
Heterocycles form by far the largest of the classical divisions of organic chemistry. Moreover,
they are of immense importance not only both biologically and industrially but to the …

Zeolite supported Brønsted-acid ionic liquids: an eco approach for synthesis of spiro [indole-pyrido [3, 2-e] thiazine] in water under ultrasonication

K Arya, DS Rawat, H Sasai - Green Chemistry, 2012 - pubs.rsc.org
A zeolite supported Brønsted-acid catalyst system has been developed using different
Brønsted-acid ionic liquids supported on ZSM-5 zeolite. Catalytic activity was tested via …

Preparation of fluorinated tetrahydropyrans and piperidines using a new nucleophilic fluorination reagent DMPU/HF

OE Okoromoba, GB Hammond, B Xu - Organic letters, 2015 - ACS Publications
DMPU/HF (HF content 65 wt%/wt) is an ideal nucleophilic fluorination reagent for the
diastereoselective synthesis of substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines …

Stereoselective syntheses of (−)-tetrahydrolipstatin via Prins cyclisations

JS Yadav, MS Reddy, AR Prasad - Tetrahedron letters, 2006 - Elsevier
Stereoselective syntheses of (−)-tetrahydrolipstatin have been achieved via two divergent
approaches through Prins cyclisations as the key steps. PCC mediated oxidative cleavage …

A convergent route to β-hydroxy δ-lactones through Prins cyclisation as the key step: synthesis of (+)-prelactones B, C and V

JS Yadav, MS Reddy, AR Prasad - Tetrahedron letters, 2005 - Elsevier
Reactions of homoallylic alcohols with aldehydes in the presence of acid catalysts gave
multisubstituted tetrahydropyrans with the creation of one to three new stereogenic centres …

Stereoselective synthesis of anti-1, 3-diol units via Prins cyclisation: application to the synthesis of (−)-sedamine

JS Yadav, MS Reddy, PP Rao, AR Prasad - Tetrahedron letters, 2006 - Elsevier
The scope of the Prins cyclisation, the higher stereoselective synthesis of multisubstituted
tetrahydropyrans from aldehydes and homoallylic alcohols, is expanded. A new approach …

Facile and highly efficient synthesis of fluorinated heterocycles via Prins cyclization in ionic liquid hydrogen fluoride salts

Y Kishi, H Nagura, S Inagi, T Fuchigami - Chemical communications, 2008 - pubs.rsc.org
Facile and highly efficient synthesis of fluorinated heterocycles via Prins cyclization in ionic
liquid hydrogen fluoride salts - Chemical Communications (RSC Publishing) DOI:10.1039/B806389C …