Literature DB >> 12137521

Highly enantioselective epoxidation of alpha, beta-unsaturated esters by chiral dioxirane.

Xin-Yan Wu1, Xuegong She, Yian Shi.   

Abstract

This paper describes a highly enantioselective epoxidation of alpha,beta-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82-98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's.

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Year:  2002        PMID： 12137521     DOI： 10.1021/ja020478y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  9 in total

1.  Iron(II)-Catalyzed Asymmetric Epoxidation of Trisubstituted α,β-Unsaturated Esters.

Authors:  Lan Luo; Hisashi Yamamoto
Journal:  European J Org Chem       Date:  2014-12

2.  Iron-catalyzed asymmetric epoxidation of β,β-disubstituted enones.

Authors:  Yasuhiro Nishikawa; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2011-05-16       Impact factor: 15.419

Review 3.  Synthesis and Applications of Carbohydrate-Based Organocatalysts.

Authors:  Elżbieta Wojaczyńska; Franz Steppeler; Dominika Iwan; Marie-Christine Scherrmann; Alberto Marra
Journal:  Molecules       Date:  2021-11-30       Impact factor: 4.411

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

Authors:  Bin Wang; Xin-Yan Wu; O Andrea Wong; Brian Nettles; Mei-Xin Zhao; Dajun Chen; Yian Shi
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

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

Authors:  O Andrea Wong; Yian Shi
Journal:  J Org Chem       Date:  2009-11-06       Impact factor: 4.354

6.  Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation.

Authors:  Daniel Rackl; Viktor Kais; Eugen Lutsker; And Oliver Reiser
Journal:  European J Org Chem       Date:  2017-02-28

7.  Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core.

Authors:  Sangbin Park; Gyumin Kang; Chansu Kim; Dongwook Kim; Sunkyu Han
Journal:  Nat Commun       Date:  2022-09-02       Impact factor: 17.694

8.  Kinetic resolution in asymmetric epoxidation using iminium salt catalysis.

Authors:  Philip C Bulman Page; Louise F Appleby; Yohan Chan; David P Day; Benjamin R Buckley; Alexandra M Z Slawin; Steven M Allin; Michael J McKenzie
Journal:  J Org Chem       Date:  2013-08-06       Impact factor: 4.354

9.  Optimization of Two Steps in Scale-Up Synthesis of Nannocystin A.

Authors:  Tingrong Zhang; Shaojie Miao; Mingxiao Zhang; Wenjie Liu; Liang Wang; Yue Chen
Journal:  Mar Drugs       Date:  2021-03-31       Impact factor: 5.118
  9 in total

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