Literature DB >> 26419786

Gold(I)-Catalyzed Enantioselective Desymmetrization of 1,3-Diols through Intramolecular Hydroalkoxylation of Allenes.

Weiwei Zi1, F Dean Toste2.   

Abstract

A gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols was achieved by intramolecular hydroalkoxylation of allenes. The catalyst system 3-F-dppe(AuCl)2/(R)-C8-TRIPAg proved to be specifically efficient to promote the desymmetrizing cyclization of 2-aryl-1,3-diols, which have proven challenging substrates in previous reports. Multisubstituted tetrahydrofurans were prepared in good yield with good enantioselectivity and diastereoselectivity by this method.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenes; desymmetrization; enantioselective synthesis; gold; hydroalkoxylation

Mesh：

Substances：

Year:  2015        PMID： 26419786      PMCID： PMC4715695          DOI： 10.1002/anie.201508331

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  35 in total

1.  Gold(I)-catalyzed dynamic kinetic enantioselective intramolecular hydroamination of allenes.

Authors:  Zhibin Zhang; Christopher F Bender; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2007-10-30       Impact factor: 15.419

2.  Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors:  Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-09-21       Impact factor: 15.419

3.  Organocatalytic enantioselective acyl transfer onto racemic as well as meso alcohols, amines, and thiols.

Authors:  Christian E Müller; Peter R Schreiner
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-27       Impact factor: 15.336

4.  Counterion-mediated hydrogen-bonding effects: mechanistic study of gold(I)-catalyzed enantioselective hydroamination of allenes.

Authors:  Ji Hye Kim; Sung-Woo Park; Sae Rom Park; Sungyul Lee; Eun Joo Kang
Journal:  Chem Asian J       Date:  2011-07-06

5.  Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

Authors:  Timothy J Brown; Dieter Weber; Michel R Gagné; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2012-05-29       Impact factor: 15.419

6.  Chiral phosphoric acid catalyzed highly enantioselective desymmetrization of 2-substituted and 2,2-disubstituted 1,3-diols via oxidative cleavage of benzylidene acetals.

Authors:  Shan-Shui Meng; Yong Liang; Kou-Sen Cao; Lufeng Zou; Xing-Bang Lin; Hui Yang; K N Houk; Wen-Hua Zheng
Journal:  J Am Chem Soc       Date:  2014-08-25       Impact factor: 15.419

7.  Enantio- and diastereoselective assembly of tetrahydrofuran and tetrahydropyran skeletons with all-carbon-substituted quaternary stereocenters.

Authors:  Zhilong Chen; Jianwei Sun
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-19       Impact factor: 15.336

8.  Gold(I)-Catalyzed Hydroarylation of Allenes with Indoles.

Authors:  Kristina L Toups; Gordon T Liu; Ross A Widenhoefer
Journal:  J Organomet Chem       Date:  2009-02-15       Impact factor: 2.369

9.  Gold(I)-catalyzed enantioselective synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines.

Authors:  R L Lalonde; Z J Wang; M Mba; A D Lackner; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

10.  Pd-catalyzed desymmetric intramolecular O-arylation reaction: enantioselective synthesis of (3,4-dihydro-2H-chromen-3-yl)methanols.

Authors:  Wenqiang Yang; Jiajie Yan; Yan Long; Shasha Zhang; Jianguang Liu; Youlin Zeng; Qian Cai
Journal:  Org Lett       Date:  2013-11-21       Impact factor: 6.005
View more
  7 in total

1.  Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers.

Authors:  Dake Chen; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2020-06-04       Impact factor: 6.005

Review 2.  Catalytic Asymmetric Hydroalkoxylation of C-C Multiple Bonds.

Authors:  Jennifer L Kennemur; Rajat Maji; Manuel J Scharf; Benjamin List
Journal:  Chem Rev       Date:  2021-12-03       Impact factor: 60.622

3.  H-Bonded Counterion-Directed Enantioselective Au(I) Catalysis.

Authors:  Allegra Franchino; Àlex Martí; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2022-02-09       Impact factor: 15.419

4.  Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature.

Authors:  Piyatida Klumphu; Camille Desfeux; Yitao Zhang; Sachin Handa; Fabrice Gallou; Bruce H Lipshutz
Journal:  Chem Sci       Date:  2017-07-20       Impact factor: 9.825

5.  Selenide-catalyzed enantioselective synthesis of trifluoromethylthiolated tetrahydronaphthalenes by merging desymmetrization and trifluoromethylthiolation.

Authors:  Jie Luo; Qingxiang Cao; Xiaohui Cao; Xiaodan Zhao
Journal:  Nat Commun       Date:  2018-02-06       Impact factor: 14.919

6.  Construction of spirocarbocycles via gold-catalyzed intramolecular dearomatization of naphthols.

Authors:  Wen-Ting Wu; Ren-Qi Xu; Liming Zhang; Shu-Li You
Journal:  Chem Sci       Date:  2016-02-02       Impact factor: 9.825

7.  Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination.

Authors:  Zhang-Long Yu; Yong-Feng Cheng; Na-Chuan Jiang; Jian Wang; Li-Wen Fan; Yue Yuan; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu
Journal:  Chem Sci       Date:  2020-05-20       Impact factor: 9.825
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.