Literature DB >> 15280968

Iodine electrophiles in stereoselective reactions: recent developments and synthetic applications.

Andrew N French1, Stewart Bissmire, Thomas Wirth.   

Abstract

The regio- and stereocontrolled functionalisation of carbon-carbon double bonds bears enormous potential in organic synthesis. This area has been extensively studied and reviewed as alkenes are amongst the most important starting materials for synthetic chemists, accessible in many varieties and in large quantities. We focus in this tutorial review only on recent developments using iodine electrophiles for the functionalisation of alkenes although transition-mediated reactions and functionalisations with chalcogen electrophiles also play an important role. New synthetic applications using this methodology showing scope and limitations of iodine-mediated processes also within the context of other electrophilic reactions are highlighted.

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Year:  2004        PMID: 15280968     DOI: 10.1039/b310389g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  18 in total

1.  Lewis base catalysis of bromo- and iodolactonization, and cycloetherification.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Proc Natl Acad Sci U S A       Date:  2010-08-12       Impact factor: 11.205

2.  Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes.

Authors:  Bradley B Gilbert; Stanley T-C Eey; Pavel Ryabchuk; Olivia Garry; Scott E Denmark
Journal:  Tetrahedron       Date:  2019-06-01       Impact factor: 2.457

3.  A stereoselective intramolecular halo-etherification of chiral enamides in the synthesis of halogenated cyclic ethers.

Authors:  Changhong Ko; Richard P Hsung; Ziyad F Al-Rashid; John B Feltenberger; Ting Lu; Jin-Haek Yang; Yonggang Wei; Craig A Zificsak
Journal:  Org Lett       Date:  2007-10-02       Impact factor: 6.005

Review 4.  Chemistry of polyvalent iodine.

Authors:  Viktor V Zhdankin; Peter J Stang
Journal:  Chem Rev       Date:  2008-12       Impact factor: 60.622

5.  Biomimetic Desymmetrization of a Carboxylic Acid.

Authors:  Matthew T Knowe; Michael W Danneman; Sarah Sun; Maren Pink; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2018-02-05       Impact factor: 15.419

Review 6.  Catalytic, asymmetric halofunctionalization of alkenes--a critical perspective.

Authors:  Scott E Denmark; William E Kuester; Matthew T Burk
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-25       Impact factor: 15.336

7.  Tertiary aminourea-catalyzed enantioselective iodolactonization.

Authors:  Gemma E Veitch; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2010-09-24       Impact factor: 15.336

Review 8.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

9.  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

Review 10.  Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.

Authors:  Alexander J Cresswell; Stanley T-C Eey; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-02       Impact factor: 15.336

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