Literature DB >> 23406082

Catalytic enantioselective epoxidation of tertiary allylic and homoallylic alcohols.

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

Abstract

An efficient and versatile method for the enantioselective epoxidation of both tertiary allylic and homoallylic alcohols catalyzed by Hf(IV)-bishydroxamic acid (BHA) complexes is described. Asymmetric epoxidation, kinetic resolution, and desymmetrization have been developed, demonstrating the flexible nature of the Hf(IV)-BHA system. This is the first report in which these substrates were obtained with enantioselectivities of up to 99%.

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Year:  2013        PMID： 23406082      PMCID： PMC3625140          DOI： 10.1021/ja401182a

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


  14 in total

1.  Recent advances in catalytic asymmetric epoxidation using the environmentally benign oxidant hydrogen peroxide and its derivatives.

Authors:  Giorgio De Faveri; Gennadiy Ilyashenko; Michael Watkinson
Journal:  Chem Soc Rev       Date:  2010-11-15       Impact factor: 54.564

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.  Oxidation catalysis of Nb(salan) complexes: asymmetric epoxidation of allylic alcohols using aqueous hydrogen peroxide as an oxidant.

Authors:  Hiromichi Egami; Takuya Oguma; Tsutomu Katsuki
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

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.  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

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

Authors:  Haruna Tanaka; Hiroaki Nishikawa; Tatsuya Uchida; Tsutomu Katsuki
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

7.  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

8.  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

9.  Catalytic enantioselective epoxidation of homoallylic alcohols by chiral zirconium complexes.

Authors:  Takahiro Okachi; Norio Murai; Makoto Onaka
Journal:  Org Lett       Date:  2003-01-09       Impact factor: 6.005

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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  10 in total

1.  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

2.  Synthesis of virtually enantiopure aminodiols with three adjacent stereogenic centers by epoxidation and ring-opening.

Authors:  Lan Luo; Hisashi Yamamoto
Journal:  Org Biomol Chem       Date:  2015-10-06       Impact factor: 3.876

3.  Ten years of research in Chicago.

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

4.  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

5.  Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters.

Authors:  Shen Qu; Samuel M Smith; Víctor Laina-Martín; Rifahath M Neyyappadath; Mark D Greenhalgh; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2020-07-16       Impact factor: 15.336

6.  Kinetic resolution of racemic tertiary allylic alcohols through SN2' reaction using a chiral bisphosphoric acid/silver(i) salt co-catalyst system.

Authors:  Satavisha Kayal; Jun Kikuchi; Naoya Shinagawa; Shigenobu Umemiya; Masahiro Terada
Journal:  Chem Sci       Date:  2022-07-20       Impact factor: 9.969

7.  Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.

Authors:  Shengtong Niu; Hao Zhang; Weici Xu; Prasanta Ray Bagdi; Guoxiang Zhang; Jinggong Liu; Shuang Yang; Xinqiang Fang
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919

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

10.  Experimental lineage and functional analysis of a remotely directed peptide epoxidation catalyst.

Authors:  Phillip A Lichtor; Scott J Miller
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419
  10 in total

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