Literature DB >> 23899320

One-pot anti-Markovnikov hydroamination of unactivated alkenes by hydrozirconation and amination.

Alexandra E Strom1, John F Hartwig.   

Abstract

A one-pot anti-Markovnikov hydroamination of alkenes is reported. The synthesis of primary and secondary amines from unactivated olefins was accomplished in the presence of a variety of functional groups. Hydrozirconation, followed by amination with nitrogen electrophiles, provides exclusive anti-Markovnikov selectivity. Most products are isolated in high yields without the use of column chromatography.

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Year:  2013        PMID： 23899320      PMCID： PMC3800136          DOI： 10.1021/jo401498w

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  13 in total

1.  Metal-Initiated Amination of Alkenes and Alkynes.

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Review 2.  Hydroamination: direct addition of amines to alkenes and alkynes.

Authors:  Thomas E Müller; Kai C Hultzsch; Miguel Yus; Francisco Foubelo; Mizuki Tada
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3.  2-Allylphenyl glycosides as glycosyl donors for sugar coupling.

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4.  Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines.

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5.  Synthesis of tertiary alkyl amines from terminal alkenes: copper-catalyzed amination of alkyl boranes.

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Authors:  Jason A Bexrud; Patrick Eisenberger; David C Leitch; Philippa R Payne; Laurel L Schafer
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

7.  Neuroprotective effects of N-alkyl-1,2,4-oxadiazolidine-3,5-diones and their corresponding synthetic intermediates N-alkylhydroxylamines and N-1-alkyl-3-carbonyl-1-hydroxyureas against in vitro cerebral ischemia.

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Journal:  ChemMedChem       Date:  2010-01       Impact factor: 3.466

8.  Iridium-catalyzed regio- and enantioselective N-allylation of indoles.

Authors:  Levi M Stanley; John F Hartwig
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9.  Direct stereospecific amination of alkyl and aryl pinacol boronates.

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  9 in total

1.  Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids.

Authors:  Zhiwei Ma; Zhe Zhou; László Kürti
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-12       Impact factor: 15.336

Review 2.  Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.

Authors:  Beau P Pritchett; Brian M Stoltz
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3.  Enantioselective Catalysis Coupled with Stereodivergent Cyclization Strategies Enables Rapid Syntheses of (+)-Limaspermidine and (+)-Kopsihainanine A.

Authors:  Beau P Pritchett; Etienne J Donckele; Brian M Stoltz
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4.  Enantioselective hydroamination of unactivated terminal alkenes.

Authors:  Senjie Ma; Yumeng Xi; Haoyu Fan; Sven Roediger; John F Hartwig
Journal:  Chem       Date:  2022-01-11       Impact factor: 25.832

5.  Site-selective amination and/or nitrilation via metal-free C(sp2)-C(sp3) cleavage of benzylic and allylic alcohols.

Authors:  Raghunath Reddy Anugu; John R Falck
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6.  Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (-)-Goniomitine, (+)-Aspidospermidine, and (-)-Quebrachamine.

Authors:  Beau P Pritchett; Jun Kikuchi; Yoshitaka Numajiri; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-26       Impact factor: 15.336

7.  Catalytic Enantioselective Synthesis of Acyclic Quaternary Centers: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Acyclic Enol Carbonates.

Authors:  Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2018-08-02       Impact factor: 15.419

8.  Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes.

Authors:  Matthew H Gieuw; Shuming Chen; Zhihai Ke; K N Houk; Ying-Yeung Yeung
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9.  Persulfate Reaction in a Hair-Bleaching Formula: Unveiling the Unconventional Reactivity of 1,13-Diamino-4,7,10-Trioxatridecane.

Authors:  Emanuele M Gargano; Giuseppe F Mangiatordi; Ingo Weber; Carsten Goebel; Domenico Alberga; Orazio Nicolotti; Wolfgang Ruess; Stefan Wierlacher
Journal:  ChemistryOpen       Date:  2018-03-25       Impact factor: 2.911
  9 in total

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