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Literature DB >> 17458998

Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane.

Abstract

This paper describes a highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketone 2 as catalyst and Oxone as oxidant to form cis-propargyl epoxides in high ee's. The interaction between the alkyne group of the substrate and the oxazolidinone moiety of the ketone catalyst as well as the interactions between the substituents on enynes and the oxazolidinone moiety of the ketone catalyst are important for the stereodifferentiation.

Entities: Chemical

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Year: 2007 PMID： 17458998 DOI： 10.1021/jo070205r

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

9 in total

Review 1. Rearrangements of organic peroxides and related processes.

Authors: Ivan A Yaremenko; Vera A Vil'; Dmitry V Demchuk; Alexander O Terent'ev
Journal: Beilstein J Org Chem Date: 2016-08-03 Impact factor: 2.883

2. Scalable and efficient synthesis of the mycolactone core.

Authors: Katrina L Jackson; Wenju Li; Chi-Li Chen; Yoshito Kishi
Journal: Tetrahedron Date: 2010-03-27 Impact factor: 2.457

3. Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.

Authors: Kun Huang; Haiyang Wang; Viatcheslav Stepanenko; Melvin De Jesús; Carilyn Torruellas; Wildeliz Correa; Margarita Ortiz-Marciales
Journal: J Org Chem Date: 2011-02-04 Impact factor: 4.354

9. Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.

Authors: Hai-Yang Wang; Kun Huang; Melvin De Jesús; Sandraliz Espinosa; Luis E Piñero-Santiago; Charles L Barnes; Margarita Ortiz-Marciales
Journal: Tetrahedron Asymmetry Date: 2016-02-15

9 in total

Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane.

Review 1. Rearrangements of organic peroxides and related processes.

2. Scalable and efficient synthesis of the mycolactone core.

3. Chiral epoxides via borane reduction of 2-haloketones catalyzed by spiroborate ester: application to the synthesis of optically pure 1,2-hydroxy ethers and 1,2-azido alcohols.

Review 4. Synthesis and Applications of Carbohydrate-Based Organocatalysts.

5. Asymmetric epoxidation of 1,1-disubstituted terminal olefins by chiral dioxirane via a planar-like transition state.

6. A diacetate ketone-catalyzed asymmetric epoxidation of olefins.

7. Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane.

8. Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity.

9. Synthesis of enantiopure 1,2-azido and 1,2-amino alcohols via regio- and stereoselective ring-opening of enantiopure epoxides by sodium azide in hot water.