Literature DB >> 18850744

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

Bin Wang1, O Andrea Wong, Mei-Xin Zhao, Yian Shi.   

Abstract

Various 1,1-disubstituted terminal olefins have been investigated for asymmetric epoxidation using chiral ketone catalysts. Up to 88% ee has been achieved with a lactam ketone, and a planar transition state is likely to be a major reaction pathway.

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Year:  2008        PMID： 18850744      PMCID： PMC2736380          DOI： 10.1021/jo801576k

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


  28 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.  Functionalized iminium salt systems for catalytic asymmetric epoxidation.

Authors:  P C Page; G A Rassias; D Barros; A Ardakani; B Buckley; D Bethell; T A Smith; A M Slawin
Journal:  J Org Chem       Date:  2001-10-19       Impact factor: 4.354

4.  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

5.  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

6.  Practical asymmetric synthesis of the herbicide (S)-indanofan via lipase-catalyzed kinetic resolution of a diol and stereoselective acid-catalyzed hydrolysis of a chiral epoxide.

Authors:  Ken Tanaka; Kenji Yoshida; Chiduko Sasaki; Yasuko T Osano
Journal:  J Org Chem       Date:  2002-05-03       Impact factor: 4.354

7.  Highly efficient catalytic asymmetric epoxidation of allylic alcohols by an oxovanadium-substituted polyoxometalate with a regenerative TADDOL-derived hydroperoxide.

Authors:  Waldemar Adam; Paul L Alsters; Ronny Neumann; Chantu R Saha-Möller; Dieter Seebach; Rui Zhang
Journal:  Org Lett       Date:  2003-03-06       Impact factor: 6.005

8.  Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

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

9.  Ketone-catalyzed asymmetric epoxidation reactions.

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

10.  Organocatalysis of asymmetric epoxidation mediated by iminium salts under nonaqueous conditions.

Authors:  Philip C Bulman Page; David Barros; Benjamin R Buckley; Adel Ardakani; Brian A Marples
Journal:  J Org Chem       Date:  2004-05-14       Impact factor: 4.354
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  9 in total

1.  An organocatalytic asymmetric chlorolactonization.

Authors:  Daniel C Whitehead; Roozbeh Yousefi; Arvind Jaganathan; Babak Borhan
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

2.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

3.  Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.

Authors:  Brandon A Vara; Thomas J Struble; Weiwei Wang; Mark C Dobish; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2015-06-03       Impact factor: 15.419

4.  Zirconium(IV)- and hafnium(IV)-catalyzed highly enantioselective epoxidation of homoallylic and bishomoallylic alcohols.

Authors:  Zhi Li; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

5.  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

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.  Enantioselective CuH-catalyzed anti-Markovnikov hydroamination of 1,1-disubstituted alkenes.

Authors:  Shaolin Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2014-10-29       Impact factor: 15.419

8.  Enantioselective synthesis of 2,2-disubstituted terminal epoxides via catalytic asymmetric Corey-Chaykovsky epoxidation of ketones.

Authors:  Toshihiko Sone; Akitake Yamaguchi; Shigeki Matsunaga; Masakatsu Shibasaki
Journal:  Molecules       Date:  2012-02-07       Impact factor: 4.411

9.  Stereocontrolled synthesis and functionalization of cyclobutanes and cyclobutanones.

Authors:  Francesco Secci; Angelo Frongia; Pier Paolo Piras
Journal:  Molecules       Date:  2013-12-13       Impact factor: 4.411
  9 in total

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