Literature DB >> 24697791

Catalytic asymmetric bromoetherification and desymmetrization of olefinic 1,3-diols with C2-symmetric sulfides.

Zhihai Ke1, Chong Kiat Tan, Feng Chen, Ying-Yeung Yeung.   

Abstract

An enantioselective and highly diastereoselective bromoetherification and desymmetrization of olefinic 1,3-diols has been developed using a C2-symmetric cyclic sulfide catalyst. This methodology has been successfully applied to the synthesis of the key intermediate of an orally active antifungal drug posaconazole (Noxafil).

Entities:  

Year:  2014        PMID: 24697791     DOI: 10.1021/ja5029155

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


  14 in total

1.  Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO2-Capture: Discovery, Development, and Mechanism.

Authors:  Roozbeh Yousefi; Thomas J Struble; Jenna L Payne; Mahesh Vishe; Nathan D Schley; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-12-24       Impact factor: 15.419

2.  Highly Stereoselective Intermolecular Haloetherification and Haloesterification of Allyl Amides.

Authors:  Bardia Soltanzadeh; Arvind Jaganathan; Richard J Staples; Babak Borhan
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-25       Impact factor: 15.336

3.  Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes.

Authors:  Dietrich Böse; Scott E Denmark
Journal:  Synlett       Date:  2017-11-13       Impact factor: 2.454

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

Authors:  Weiwei Zi; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-30       Impact factor: 15.336

5.  Nonenzymatic enantioselective synthesis of all-carbon quaternary centers through desymmetrization.

Authors:  Kimberly S Petersen
Journal:  Tetrahedron Lett       Date:  2015-11-25       Impact factor: 2.415

Review 6.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

7.  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

8.  Oxoammonium salts are catalysing efficient and selective halogenation of olefins, alkynes and aromatics.

Authors:  Weijin Wang; Xinyao Li; Xiaoxue Yang; Lingsheng Ai; Zhiwen Gong; Ning Jiao; Song Song
Journal:  Nat Commun       Date:  2021-06-23       Impact factor: 14.919

9.  Absolute and relative facial selectivities in organocatalytic asymmetric chlorocyclization reactions.

Authors:  Nastaran Salehi Marzijarani; Roozbeh Yousefi; Arvind Jaganathan; Kumar Dilip Ashtekar; James E Jackson; Babak Borhan
Journal:  Chem Sci       Date:  2018-01-02       Impact factor: 9.825

10.  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

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