Literature DB >> 19388627

A diacetate ketone-catalyzed asymmetric epoxidation of olefins.

Bin Wang1, Xin-Yan Wu, O Andrea Wong, Brian Nettles, Mei-Xin Zhao, Dajun Chen, Yian Shi.   

Abstract

A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient alpha,beta-unsaturated esters as well as certain cis olefins.

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Year:  2009        PMID： 19388627      PMCID： PMC2749516          DOI： 10.1021/jo900330n

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


  24 in total

1.  Enantioselective epoxidation of terminal olefins by chiral dioxirane.

Authors:  H Tian; X She; J Xu; Y Shi
Journal:  Org Lett       Date:  2001-06-14       Impact factor: 6.005

Review 2.  Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.

Authors:  O Andrea Wong; Yian Shi
Journal:  Chem Rev       Date:  2008-07-01       Impact factor: 60.622

3.  Practical synthesis of Shi's diester fructose derivative for catalytic asymmetric epoxidation of alkenes.

Authors:  N Nieto; P Molas; J Benet-Buchholz; A Vidal-Ferran
Journal:  J Org Chem       Date:  2005-11-25       Impact factor: 4.354

4.  Electronic probing of ketone catalysts for asymmetric epoxidation. Search for more robust catalysts.

Authors:  H Tian; X She; Y Shi
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

5.  Regio- and enantioselective epoxidation of dienes by a chiral dioxirane: synthesis of optically active vinyl cis-epoxides.

Authors:  Christopher P Burke; Yian Shi
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-03       Impact factor: 15.336

6.  Designing new chiral ketone catalysts. Asymmetric epoxidation of cis-olefins and terminal olefins.

Authors:  Hongqi Tian; Xuegong She; Hongwu Yu; Lianhe Shu; Yian Shi
Journal:  J Org Chem       Date:  2002-04-19       Impact factor: 4.354

7.  Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

Authors:  Yian Shi
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

8.  Ketone-catalyzed asymmetric epoxidation reactions.

Authors:  Dan Yang
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

9.  A cyclodextrin-modified ketoester for stereoselective epoxidation of alkenes.

Authors:  Wing-Kei Chan; Wing-Yiu Yu; Chi-Ming Che; Man-Kin Wong
Journal:  J Org Chem       Date:  2003-08-22       Impact factor: 4.354

10.  Asymmetric epoxidation catalyzed by N-aryl-substituted oxazolidinone-containing ketones: further evidence for electronic effects.

Authors:  Lianhe Shu; Pingzhen Wang; Yonghong Gan; Yian Shi
Journal:  Org Lett       Date:  2003-02-06       Impact factor: 6.005
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  10 in total

1.  Total Synthesis of the Marine Ladder Polyether Gymnocin B.

Authors:  Satapanawat Sittihan; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2019-07-08       Impact factor: 15.419

2.  Function-Oriented Investigations of a Peptide-Based Catalyst that Mediates Enantioselective Allylic Alcohol Epoxidation.

Authors:  Nadia C Abascal; Phillip A Lichtor; Michael W Giuliano; Scott J Miller
Journal:  Chem Sci       Date:  2014-11-01       Impact factor: 9.825

3.  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

4.  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

5.  Total synthesis of the protein phosphatase 2A inhibitor lactodehydrothyrsiferol.

Authors:  Dane J Clausen; Shuangyi Wan; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2011-04-21       Impact factor: 15.336

Review 6.  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

7.  Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins.

Authors:  Bing-Feng Sun; Ran Hong; Yan-Biao Kang; Li Deng
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

8.  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

9.  Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters.

Authors:  C Guy Goodman; Dung T Do; Jeffrey S Johnson
Journal:  Org Lett       Date:  2013-04-30       Impact factor: 6.005

10.  Studies on asymmetric total synthesis of (-)-β-hydrastine via a chiral epoxide ring-opening cascade cyclization strategy.

Authors:  Jihui Li; Tianxiao Wu; Xinjing Song; Yang Zheng; Jiaxin Meng; Qiaohua Qin; Yongxiang Liu; Dongmei Zhao; Maosheng Cheng
Journal:  RSC Adv       Date:  2020-05-19       Impact factor: 4.036
  10 in total

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