Recent Advances in Inverse-Electron-Demand Hetero-Diels–Alder Reactions of 1-Oxa-1,3-ButadienesReport as inadecuate




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Topics in Current Chemistry

, 374:24

First Online: 20 April 2016Received: 21 December 2015Accepted: 11 April 2016DOI: 10.1007-s41061-016-0026-2

Cite this article as: Pałasz, A. Top Curr Chem Z 2016 374: 24. doi:10.1007-s41061-016-0026-2

Abstract

This review is an endeavor to highlight the progress in the inverse-electron-demand hetero-Diels–Alder reactions of 1-oxa-1,3-butadienes in recent years. The huge number of examples of 1-oxadienes cycloadditions found in the literature clearly demonstrates the incessant importance of this transformation in pyran ring synthesis. This type of reaction is today one of the most important methods for the synthesis of dihydropyrans which are the key building blocks in structuring of carbohydrate and other natural products. Two different modes, inter- and intramolecular, of inverse-electron-demand hetero-Diels–Alder reactions of 1-oxadienes are discussed. The domino Knoevenagel hetero-Diels–Alder reactions are also described. In recent years the use of chiral Lewis acids, chiral organocatalysts, new optically active heterodienes or dienophiles have provided enormous progress in asymmetric synthesis. Solvent-free and aqueous hetero-Diels–Alder reactions of 1-oxabutadienes were also investigated. The reactivity of reactants, selectivity of cycloadditions, and chemical stability in aqueous solutions and under physiological conditions were taken into account to show the potential application of the described reactions in bioorthogonal chemistry. New bioorthogonal ligation by click inverse-electron-demand hetero-Diels–Alder cycloaddition of in situ-generated 1-oxa-1,3-butadienes and vinyl ethers was developed. It seems that some of the hetero-Diels–Alder reactions described in this review can be applied in bioorthogonal chemistry because they are selective, non-toxic, and can function in biological conditions taking into account pH, an aqueous environment, and temperature.

KeywordsHetero-Diels–Alder reactions 1-Oxa-1,3-butadienes Dihydropyrans Domino Knoevenagel hetero-Diels–Alder reactions Bioorthogonal cycloaddition AbbreviationsAcAcetyl

iBuIsobutyl

n-Bun-Butyl

t-Butert-Butyl

S,S- t-Bu-boxS,S-tert-Butylbisoxazoline

bmimNO31-Butyl-3-methylimidazolium nitrate

BnBenzyl

BPin3-Boronopinacol

BzBenzoyl

CbBenzyloxycarbonyl

DEADiethylamine

DICN,N′-Diisopropylcarbodiimide

DMAPN,N-Ddimethyl-4-aminopyridine

DMFDimethylformamide

DMSODimethyl sulfoxide

EDDAEthylene diammonium diacetate

Eufod36,6,7,7,8,8,8-Heptafluoro-2,2-dimethyl-3,5-octanedionato europium

IBXo-Iodoxybenzoic acid

MDOModularly designed organocatalyst

MSMolecular sieves

PCCPyridinium chlorochromate

PDCPyridinium dichromate

iPrIsopropyl

TBABtetra-n-Butylammonium bromide

TBAFTetrabutylammonium fluoride

TBA-HSTetrabutylammonium hydrogen sulfate

TBDMStert-Butyldimethylsilyl

TBDPStert-Butyldiphenylsilyl

TBStert-Butyldimethylsilyl

TfTrifluoromethanesulfonyl

THFTetrahydrofuran

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Author: Aleksandra Pałasz

Source: https://link.springer.com/







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