Synthesis of New Chiral 6-Carbonyl 2,3,8,8a-Tetrahydro-7<i>H</i>-oxazolo[3,2-<i>a</i>]pyridines

Noël, Romain; Vanucci-Bacqué, Corinne; Fargeau-Bellassoued, Marie-Claude; Lhommet, G.

doi:10.1021/jo051192p

Cited by 19 publications

(12 citation statements)

References 19 publications

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“…Simple and cheap reagents, as well as quite‐high yields (61–83 %) of compounds 196 , were obvious benefits of this environmentally benign procedure as compared to other acrolein‐based reactions, which involved metal catalysts (for example, cerium (IV)), organic solvents (toluene, MeCN, CH 2 Cl 2 ), sometimes prolonged heating, and, in some cases, two‐stage operations . Notably, the application of ( S )‐2‐phenylglycinol instead of ethanolamine allowed the preparation of mixtures of enantiomers of new fused oxazolidines with enantiomeric ratios from 50:50 to 80:20 and yields of 20–75 % for the one‐pot reaction, and enantiomeric ratios from 12:88 to 92:8 and yields of 61‐96 % for the two‐stage procedure ,…”

Section: Oxazolidines (Tetrahydro‐oxazoles) and 2‐oxazolines (45‐dmentioning

confidence: 99%

Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

Keiko

Вчисло

2016

Asian J Org Chem

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The recent increasei ni nterest in the chemistry of azoles has been owing to their paramount importance in several essential fields of research, such as pharmacology, medicine, biology, the organic synthesis of fine chemicals, agriculturalc hemistry, and the chemical industry.T his Focus Review summarizes and highlights recently developed methods for the synthesis of five-membered N,N-, N,O-, andN ,Sheterocycles based on the transformations of 2-alkenals. Over the last 15 years, these reactions, which often differ from reactions involving other a,b-unsaturatedc arbonyl compoundsi nt erms of methoda nd results, have gathered significant momentum. The multitude of catalytic and tech-nological novelties discussed in this Focus Review,s uch as asymmetricm etal-and organocatalysis,o ne-pot multicomponent reactions that proceed through domino, cascade, or tandem sequences, and microwave activation,p romote the formation of ad iverse range of target products, the structures of which becomec lear from the mechanistic schemes given in this Focus Review.T he mechanisms discussed reflect great advances in the chemo-, regio-, and stereoselectivity of the reactions of 2-alkenals, which allows new azoles and related compounds (imidazoles, pyrazoles, oxazoles, thiazoles, and their hydrogenatedd erivatives) to be synthesized.[a] Prof.The ORCID identification number(s) for the author(s) of this articlecan be found under http://dx.Scheme2.One-potsynthesis of imidazoles 8 and tentativemechanism of the reaction.T s= 4-toluenesulfonyl, TMS = tert-butyltrimethylsilyl, Bn = benzyl, Lg = leaving group.Scheme3.Enantioselective synthesiso f3-hydroxyalkyl and 3-aminoalkyli midazo[1,2-a]pyridines (9)through an asymmetricorganocatalytic [3+ +2] annulation strategy.Alk = alkyl.Scheme4.One-potsynthesis of imidazole-containingc ondensed heterocycles by the reaction of 2-alkoxypropenalswith N-binucleophiles.Scheme9.Aroute to 2-(1'-alkoxyvinyl)imidazolidines 27 through the condensation of alkoxy propenals.

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Section: Oxazolidines (Tetrahydro‐oxazoles) and 2‐oxazolines (45‐dmentioning

confidence: 99%

Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

Keiko

Вчисло

2016

Asian J Org Chem

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“…This technique has been exploited for the step-wise synthesis of complex chiral piperidines 17 as well as tetrahydropyridines. 18 In addition, this catalyst system is also efficient in the condensation of aniline with β-keto ketones, providing the corresponding β-enamino ketones in high yields. 16…”

Section: Amino Addition To C=o and Cn Functional Groupsmentioning

confidence: 99%

Zinc(II) Perchlorate Hexahydrate

Lin

Liu

Feng

2014

Encyclopedia of Reagents for Organic Synthesis

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“…Lhommet and co-workers have recently exploited this technique for the stepwise synthesis of complex chiral piperidines [55] and tetrahydropyridines. [56] Moreover, a peculiar reactivity pattern was observed when the starting β-keto ester 41 bore a cyanomethyl group in the α-position (Scheme 20). In this particular case the addition of the amine occurs on the CN triple bond rather than on the C=O, and a subsequent annulation reaction gives aminopyrroles 42.…”

Section: Zinc Perchlorate Hexahydratementioning

confidence: 99%

Taking Up the Cudgels for Perchlorates: Uses and Applications in Organic Reactions under Mild Conditions

et al. 2007

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Metal perchlorates are compounds of great chemical interest since they possess some unique properties, such as high electronegativity and relatively low charge density, poor complexing ability, high solubility in various organic solvents, and kinetic stability under mild conditions. Besides providing polar media when dissolved in solvents, metal perchlorates have recently found wide employment as Lewis acid promoters in various organic transformations, both in the development of new techniques for known and widely used reactions and in promotion of new kinds of reactivity. This paper presents a general overview of the more recent uses of lithium, magnesium, zinc, and nickel perchlorates, underlining the fact that such perchlorates are quite safe chemical products under mild conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Synthesis of New Chiral 6-Carbonyl 2,3,8,8a-Tetrahydro-7H-oxazolo[3,2-a]pyridines

Abstract: [reaction: see text] The preparation of new chiral 6-carbonyl 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridines by an efficient two-step procedure is described.

Cited by 19 publications

References 19 publications

Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

Synthesis of Diheteroatomic Five‐Membered Heterocyclic Compounds from α,β‐Unsaturated Aldehydes

Zinc(II) Perchlorate Hexahydrate

Taking Up the Cudgels for Perchlorates: Uses and Applications in Organic Reactions under Mild Conditions

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