Literature DB >> 23011853

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

Scott E Denmark1, William E Kuester, Matthew T Burk.   

Abstract

Despite the fact that halogenation of alkenes has been known for centuries, enantioselective variants of this reaction have only recently been developed. In the past three years, catalytic enantioselective versions of halofunctionalizations with the four common halogens have appeared and although important breakthroughs, they represent just the very beginnings of a nascent field. This Minireview provides a critical analysis of the challenges that accompany the development of general and highly enantioselective halofunctionalization reactions. Moreover, the focus herein, diverges from previous reviews of the field by identifying the various modes of catalysis and the different strategies implemented for asymmetric induction.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID: 23011853      PMCID: PMC3529098          DOI: 10.1002/anie.201204347

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


  41 in total

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Journal:  Chem Asian J       Date:  2012-02-07

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4.  Mechanistic evaluation of the halocyclization of 4-penten-1-ol by some Bis(2-substituted pyridine) and Bis(2,6-disubstituted pyridine)bromonium triflates

Authors: 
Journal:  J Org Chem       Date:  2000-09-08       Impact factor: 4.354

5.  Enantioselective bromolactonization of conjugated (Z)-enynes.

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Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

6.  Enantioselective dichlorination of allylic alcohols.

Authors:  K C Nicolaou; Nicholas L Simmons; Yongcheng Ying; Philipp M Heretsch; Jason S Chen
Journal:  J Am Chem Soc       Date:  2011-05-10       Impact factor: 15.419

7.  Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.

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8.  N-halosuccinimide/BF3-H2O, efficient electrophilic halogenating systems for aromatics.

Authors:  G K Surya Prakash; Thomas Mathew; Dushyanthi Hoole; Pierre M Esteves; Qi Wang; Golam Rasul; George A Olah
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9.  On the absolute configurational stability of bromonium and chloronium ions.

Authors:  Scott E Denmark; Matthew T Burk; Andrew J Hoover
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  DABCO-catalyzed 1,4-bromolactonization of conjugated enynes: highly stereoselective formation of a stereogenic center and an axially chiral allene.

Authors:  Wen Zhang; Huadong Xu; Hui Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

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  61 in total

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4.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

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5.  Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis.

Authors:  Jeremy D Griffin; Cortney L Cavanaugh; David A Nicewicz
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Journal:  J Am Chem Soc       Date:  2016-10-13       Impact factor: 15.419

7.  Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.

Authors:  Brandon A Vara; Thomas J Struble; Weiwei Wang; Mark C Dobish; Jeffrey N Johnston
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8.  Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes.

Authors:  Jesse L Panger; Scott E Denmark
Journal:  Org Lett       Date:  2019-12-20       Impact factor: 6.005

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

10.  Enantioselective Synthesis of Azamerone.

Authors:  Matthew L Landry; Grace M McKenna; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2019-02-08       Impact factor: 15.419

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