Literature DB >> 22067040

Enantioselective boronate additions to N-acyl quinoliniums catalyzed by tartaric acid.

Tomohiro Kodama1, Philip N Moquist, Scott E Schaus.   

Abstract

Tartaric acid catalyzes the asymmetric addition of vinylboronates to N-acyl quinoliniums, affording highly enantioenriched dihydroquinolines. The catalyst serves to activate the boronate through a ligand-exchange reaction and generates the N-acyl quinolinium in situ from the stable quinoline-derived N,O-acetal.

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Year:  2011        PMID： 22067040      PMCID： PMC4655815          DOI： 10.1021/ol2028702

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

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6.  Activity against Mycobacterium tuberculosis of alkaloid constituents of Angostura bark, Galipea officinalis.

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7.  Enantioselective conjugate addition of boronic acids to enones catalyzed by O-monoacyltartaric acids.

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8.  Ligand-catalyzed asymmetric alkynylboration of enones: a new paradigm for asymmetric synthesis using organoboranes.

Authors:  T Robert Wu; J Michael Chong
Journal:  J Am Chem Soc       Date:  2005-03-16       Impact factor: 15.419

9.  N-carboxylic acid esters of 1,2- and 1,4-dihydroquinolines. A new class of irreversible inactivators of the catecholamine alpha receptors and potent central nervous system depressants.

Authors:  B Belleau; R Martel; G Lacasse; M Ménard; N L Weinberg; Y G Perron
Journal:  J Am Chem Soc       Date:  1968-01-31       Impact factor: 15.419

10.  The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols.

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  6 in total

1.  Enantioselective synthesis of 1,2-dihydronaphthalene-1-carbaldehydes by addition of boronates to isochromene acetals catalyzed by tartaric acid.

Authors:  Yi Luan; Keith S Barbato; Philip N Moquist; Tomohiro Kodama; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

3.  Enantioselective, nickel-catalyzed Suzuki cross-coupling of quinolinium ions.

Authors:  Jason D Shields; Derek T Ahneman; Thomas J A Graham; Abigail G Doyle
Journal:  Org Lett       Date:  2013-11-26       Impact factor: 6.005

4.  A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins.

Authors:  Nianhong Lu; Lihong Wang; Zhanshan Li; Wei Zhang
Journal:  Beilstein J Org Chem       Date:  2012-02-06       Impact factor: 2.883

5.  Catalytic Asymmetric Additions of Enol Silanes to In Situ Generated Cyclic, Aliphatic N-Acyliminium Ions.

Authors:  Oleg Grossmann; Rajat Maji; Miles H Aukland; Sunggi Lee; Benjamin List
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Review 6.  Chiral Diol-Based Organocatalysts in Enantioselective Reactions.

Authors:  Truong N Nguyen; Po-An Chen; Krit Setthakarn; Jeremy A May
Journal:  Molecules       Date:  2018-09-11       Impact factor: 4.411
  6 in total

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