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Literature DB >> 21152351

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

Allan U Barlan¹, Wei Zhang, Hisashi Yamamoto.

Abstract

In this article, we describe the development and preliminary results of our new designed C(2)-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.

Entities: Chemical

Year: 2007 PMID： 21152351 PMCID： PMC2998186 DOI： 10.1016/j.tet.2007.03.071

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

18 in total

1. Substituted benzene anions as leaving groups in the reaction of sulfinyl derivatives with grignard reagents: a new and convenient route to dialkyl sulfoxides in high enantiomeric purity

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Journal: J Org Chem Date: 2000-05-09 Impact factor: 4.354

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Authors: Julien Legros; Carsten Bolm
Journal: Angew Chem Int Ed Engl Date: 2004-08-13 Impact factor: 15.336

4. Vanadium-catalyzed sulfur oxidation/kinetic resolution in the synthesis of enantiomerically pure alkyl aryl sulfoxides.

Authors: Carmelo Drago; Lorenzo Caggiano; Richard F W Jackson
Journal: Angew Chem Int Ed Engl Date: 2005-11-11 Impact factor: 15.336

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Authors: Zaïnaba Bourhani; Andrei V Malkov
Journal: Chem Commun (Camb) Date: 2005-08-19 Impact factor: 6.222

6. 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

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. 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

9. Organocatalytic asymmetric epoxidation of olefins by chiral ketones.

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

10. Chiral hydroperoxides as oxygen source in the catalytic stereoselective epoxidation of allylic alcohols by sandwich-type polyoxometalates: control of enantioselectivity through a metal-coordinated template.

Authors: Waldemar Adam; Paul L Alsters; Ronny Neumann; Chantu R Saha-Möller; Dieter Seebach; Albert K Beck; Rui Zhang
Journal: J Org Chem Date: 2003-10-17 Impact factor: 4.354

9 in total

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

Authors: José Luis Olivares-Romero; Zhi Li; Hisashi Yamamoto
Journal: J Am Chem Soc Date: 2012-03-20 Impact factor: 15.419

2. 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

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

Authors: Bin Wang; O Andrea Wong; Mei-Xin Zhao; Yian Shi
Journal: J Org Chem Date: 2008-12-19 Impact factor: 4.354

4. Hydroxamic acids in asymmetric synthesis.

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

5. A Simple Procedure for C-C Bond Cleavage of Aromatic and Aliphatic Epoxides with Aqueous Sodium Periodate Under Ambient Conditions.

Authors: Caitlin M Binder; Darryl D Dixon; Erik Almaraz; Marcus A Tius; Bakthan Singaram
Journal: Tetrahedron Lett Date: 2008-04-21 Impact factor: 2.415

9. Molybdenum-Catalyzed Enantioselective Sulfoxidation Controlled by a Nonclassical Hydrogen Bond between Coordinated Chiral Imidazolium-Based Dicarboxylate and Peroxido Ligands.

Authors: Carlos J Carrasco; Francisco Montilla; Agustín Galindo
Journal: Molecules Date: 2018-06-30 Impact factor: 4.411