Literature DB >> 19824657

Enantioselective epoxidation of nonconjugated cis-olefins by chiral dioxirane.

Christopher P Burke1, Yian Shi.   

Abstract

A variety of nonconjugated cis-olefins has been enantioselectively epoxidized with chiral ketones 2, and up to 92% ee has been obtained. The two prochiral faces of an olefin are likely stereodifferentiated by the relative hydrophobicity of the olefin substituents and/or allylic oxygen functionality.

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Year:  2009        PMID： 19824657      PMCID： PMC2783705          DOI： 10.1021/ol901724v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  23 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

2.  Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: an effective controller system and a rational mechanistic model.

Authors:  Wei Zhang; Arindrajit Basak; Yuji Kosugi; Yujiro Hoshino; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-11       Impact factor: 15.336

3.  Titanium-catalyzed asymmetric epoxidation of non-activated olefins with hydrogen peroxide.

Authors:  Yuji Sawada; Kazuhiro Matsumoto; Tsutomu Katsuki
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  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

5.  On the biological inactivity of 4,5-dihydroxy-n-decanoic acid-4-lactones.

Authors:  U Gräfe; I Eritt
Journal:  J Antibiot (Tokyo)       Date:  1983-11       Impact factor: 2.649

6.  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

7.  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

8.  Novel catalytic kinetic resolution of racemic epoxides to allylic alcohols.

Authors:  Arnaud Gayet; Sophie Bertilsson; Pher G Andersson
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

9.  Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

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

10.  Ketone-catalyzed asymmetric epoxidation reactions.

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

1.  Synthesis of (+)-Disparlure via Enantioselective Iodolactonization.

Authors:  Daniel W Klosowski; Stephen F Martin
Journal:  Org Lett       Date:  2018-02-12       Impact factor: 6.005

2.  Stereoselective VO(acac)(2) Catalyzed Epoxidation of Acyclic Homoallylic Diols. Complementary Preparation of C2-syn-3,4-Epoxy Alcohols.

Authors:  Raúl R Rodríguez-Berríos; Gerardo Torres; José A Prieto
Journal:  Tetrahedron       Date:  2011-02-04       Impact factor: 2.457

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.  Enantioselective Halolactonization Reactions using BINOL-Derived Bifunctional Catalysts: Methodology, Diversification, and Applications.

Authors:  Daniel W Klosowski; J Caleb Hethcox; Daniel H Paull; Chao Fang; James R Donald; Christopher R Shugrue; Andrew D Pansick; Stephen F Martin
Journal:  J Org Chem       Date:  2018-05-22       Impact factor: 4.354

5.  Enantioselective iodolactonization of disubstituted olefinic acids using a bifunctional catalyst.

Authors:  Chao Fang; Daniel H Paull; J Caleb Hethcox; Christopher R Shugrue; Stephen F Martin
Journal:  Org Lett       Date:  2012-11-30       Impact factor: 6.005
  5 in total

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