Literature DB >> 22420598

Hf(IV)-catalyzed enantioselective epoxidation of N-alkenyl sulfonamides and N-tosyl imines.

José Luis Olivares-Romero1, Zhi Li, Hisashi Yamamoto.   

Abstract

Asymmetric epoxidation of allylic and homoallylic amine derivatives catalyzed by Hf(IV)-bishydroxamic acid complexes is described. Under similar conditions, aldimine and ketimine produced oxaziridines. The sulfonyl group is demonstrated to be an effective directing group for these transformations.

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Year:  2012        PMID： 22420598      PMCID： PMC3443980          DOI： 10.1021/ja211880s

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


  24 in total

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Journal:  Angew Chem Int Ed Engl       Date:  2005-07-11       Impact factor: 15.336

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3.  Photopromoted Ru-catalyzed asymmetric aerobic sulfide oxidation and epoxidation using water as a proton transfer mediator.

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Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

4.  Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation.

Authors:  Allan U Barlan; Wei Zhang; Hisashi Yamamoto
Journal:  Tetrahedron       Date:  2007-07-02       Impact factor: 2.457

5.  H-Bonding Interactions in the Epoxidation of Alkenylammonium Salts with Dimethyldioxirane and m-Chloroperbenzoic Acid: A Kinetic Study.

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Journal:  J Org Chem       Date:  1999-06-25       Impact factor: 4.354

6.  One-pot conversions of olefins to cyclic carbonates and secondary allylic and homoallylic amines to cyclic carbamates.

Authors:  Stephen G Davies; Ai M Fletcher; Wataru Kurosawa; James A Lee; Giovanna Poce; Paul M Roberts; James E Thomson; David M Williamson
Journal:  J Org Chem       Date:  2010-10-18       Impact factor: 4.354

7.  Asymmetric epoxidation of homoallylic alcohols and application in a concise total synthesis of (-)-alpha-bisabolol and (-)-8-epi-alpha-bisabolol.

Authors:  Naoya Makita; Yujiro Hoshino; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-24       Impact factor: 15.336

8.  A new approach to functionalized spiropiperidines through tandem RCM and nitrogen-directed reactions.

Authors:  Andrew S Edwards; Robert A J Wybrow; Craig Johnstone; Harry Adams; Joseph P A Harrity
Journal:  Chem Commun (Camb)       Date:  2002-07-21       Impact factor: 6.222

9.  Phosphorylated hydroxyethylamines as novel inhibitors of the bacterial cell wall biosynthesis enzymes MurC to MurF.

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Journal:  Bioorg Chem       Date:  2009-09-10       Impact factor: 5.275

10.  Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine.

Authors:  Ona Illa; Muhammad Arshad; Abel Ros; Eoghan M McGarrigle; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
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  9 in total

1.  Hydroxamic acids in asymmetric synthesis.

Authors:  Zhi Li; Hisashi Yamamoto
Journal:  Acc Chem Res       Date:  2012-11-16       Impact factor: 22.384

2.  Catalytic enantioselective epoxidation of tertiary allylic and homoallylic alcohols.

Authors:  José Luis Olivares-Romero; Zhi Li; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2013-02-19       Impact factor: 15.419

3.  Gadolinium-Catalyzed Regio- and Enantioselective Aminolysis of Aromatic trans-2,3-Epoxy Sulfonamides.

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Journal:  Angew Chem Int Ed Engl       Date:  2015-06-08       Impact factor: 15.336

4.  Ten years of research in Chicago.

Authors:  Hisashi Yamamoto
Journal:  Tetrahedron       Date:  2013-06-10       Impact factor: 2.457

5.  Advances in the chemistry of oxaziridines.

Authors:  Kevin S Williamson; David J Michaelis; Tehshik P Yoon
Journal:  Chem Rev       Date:  2014-04-22       Impact factor: 60.622

6.  Brønsted acid catalyzed phosphoramidic acid additions to alkenes: diastereo- and enantioselective halogenative cyclizations for the synthesis of C- and P-chiral phosphoramidates.

Authors:  Yasunori Toda; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2014-10-14       Impact factor: 15.419

7.  Catalytic asymmetric synthesis of CF3-substituted tertiary propargylic alcohols via direct aldol reaction of α-N3 amide.

Authors:  Hidetoshi Noda; Fuyuki Amemiya; Karin Weidner; Naoya Kumagai; Masakatsu Shibasaki
Journal:  Chem Sci       Date:  2017-03-02       Impact factor: 9.825

8.  Tungsten-catalyzed regioselective and stereospecific ring opening of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2014-05-02       Impact factor: 15.419

9.  Tungsten-catalyzed asymmetric epoxidation of allylic and homoallylic alcohols with hydrogen peroxide.

Authors:  Chuan Wang; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2014-01-21       Impact factor: 15.419
  9 in total

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