Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

Tran, Thi Thu Thuy; Ngo, Ngoc Thang; Dinh, Thi Ha; Legoupy, Stéphanie

doi:10.1002/bkcs.10270

Bulletin Korean Chem Soc

2015

DOI: 10.1002/bkcs.10270

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Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

Thi Thu Thuy Tran

Ngoc Thang Ngo

Thi Ha Dinh

et al.

Abstract: International audience
Synthesis of triazolo-cyclobutane nucleosides analogs is reported. These molecules have been obtained by a short and efficient sequence involving a click azide-alkyne cycloaddition following by cis-hydroxylation in the key step.

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“…Notably, no loss of enantio-purity was observed in these reactions. The 2-aminomethyl-1-cyclobutanol moiety has been found in a number of pharmaceutical agents …”

mentioning

confidence: 99%

Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Deng

Lee

et al. 2019

J. Am. Chem. Soc.

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Herein we describe the development of a highly selective kinetic resolution of cyclobutanones via a Rh-catalyzed "cut-and-sew" reaction with selectivity factor up to 785. This reaction takes place at room temperature with excellent efficiency. Various trans-5,6-fused bicycles and C2-substituted cyclobutanones were obtained with excellent ee's that can be further used as chiral building blocks. DFT calculations reveal the crucial roles of the DTBM-segphos ligand in stabilizing the rate-and enantioselectivity-determining C−C oxidative addition transition state via favorable ligand−substrate dispersion interactions.

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“…Notably, no loss of enantio-purity was observed in these reactions. The 2-aminomethyl-1-cyclobutanol moiety has been found in a number of pharmaceutical agents …”

mentioning

confidence: 99%

Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Deng

Lee

et al. 2019

J. Am. Chem. Soc.

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Square sugars: challenges and synthetic strategies

Hazelard

Compain

2017

Org. Biomol. Chem.

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Square sugars (4-membered ring carbohydrate mimetics) are at the intersection of several important topics concerning the recent emergence, in medicinal chemistry, of glycomimetic drugs and small ring systems. Monosaccharide mimetics containing oxetane, azetidine, thiethane or cyclobutane rings present a number of synthetic challenges that are a powerful driving force for innovation in organic synthesis. In addition to the inherent issues associated with 4-membered rings, the high density of functional groups and asymmetric centres found in glycomimetics further complicates the matter and requires efficient stereoselective methodologies. The purpose of this review is to present an overview of the elegant strategies that have been developed to synthesize the different types of square sugars.

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Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

Abstract: International audience
Synthesis of triazolo-cyclobutane nucleosides analogs is reported. These molecules have been obtained by a short and efficient sequence involving a click azide-alkyne cycloaddition following by cis-hydroxylation in the key step.

Cited by 2 publications

References 30 publications

Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Square sugars: challenges and synthetic strategies

Contact Info

Product

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Synthesis of Novel Triazolo Cyclobutane Nucleoside Analogs

Abstract: International audienceSynthesis of triazolo-cyclobutane nucleosides analogs is reported. These molecules have been obtained by a short and efficient sequence involving a click azide-alkyne cycloaddition following by cis-hydroxylation in the key step.

Cited by 2 publications

References 30 publications

Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Kinetic Resolution via Rh-Catalyzed C–C Activation of Cyclobutanones at Room Temperature

Square sugars: challenges and synthetic strategies

Contact Info

Product

Resources

About

Abstract: International audience
Synthesis of triazolo-cyclobutane nucleosides analogs is reported. These molecules have been obtained by a short and efficient sequence involving a click azide-alkyne cycloaddition following by cis-hydroxylation in the key step.