Literature DB >> 18288864

Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles.

Zhi Wang1, Yong-Tao Cui, Zhao-Bing Xu, Jin Qu.   

Abstract

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 degrees C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.

Entities:  

Year:  2008        PMID： 18288864     DOI： 10.1021/jo702401t

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


  15 in total

Review 1.  The development of endo-selective epoxide-opening cascades in water.

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2.  Sulfonylation-induced N- to O-acetyl migration in 2-acetamidoethanol derivatives.

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3.  Synthesis of the C'D'E'F' domain of maitotoxin.

Authors:  K C Nicolaou; Jae Hong Seo; Tsuyoshi Nakamura; Robert J Aversa
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

4.  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

Review 5.  Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

6.  Structure-activity relationship and in vitro and in vivo evaluation of the potent cytotoxic anti-microtubule agent N-(4-methoxyphenyl)-N,2,6-trimethyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-aminium chloride and its analogues as antitumor agents.

Authors:  Aleem Gangjee; Ying Zhao; Sudhir Raghavan; Cristina C Rohena; Susan L Mooberry; Ernest Hamel
Journal:  J Med Chem       Date:  2013-08-29       Impact factor: 7.446

7.  New strategy for the synthesis of substituted morpholines.

Authors:  Matthew L Leathen; Brandon R Rosen; John P Wolfe
Journal:  J Org Chem       Date:  2009-07-17       Impact factor: 4.354

8.  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.  Synthesis of the EFG Framework of Tamulamides A and B.

Authors:  Elizabeth H Kelley; Timothy F Jamison
Journal:  Org Lett       Date:  2019-09-16       Impact factor: 6.005

Review 10.  Organocatalyzed enantioselective desymmetrization of aziridines and epoxides.

Authors:  Ping-An Wang
Journal:  Beilstein J Org Chem       Date:  2013-08-15       Impact factor: 2.883
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