Literature DB >> 25382939

Controlling Enantioselectivity in Additions to Cyclic Oxocarbenium Ions via Transition Metal Catalysis.

Mary P Watson1, Prantik Maity1.   

Abstract

Controlling enantioselectivity in additions to oxocarbenium ions remains a challenge in asymmetric catalysis. By catalytically generating a chiral organometallic intermediate, a copper acetylide, we have developed a novel approach for additions of carbon nucleophiles to cyclic oxocarbenium ions in high enantioselectivities and yields.

Entities:  

Keywords:  alkyne addition; asymmetric catalysis; enantioselectivity; oxocarbenium ions; transition metals

Year:  2012        PMID： 25382939      PMCID： PMC4220455          DOI： 10.1055/s-0031-1290697

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  30 in total

1.  Titanium(IV)-catalyzed dynamic kinetic asymmetric transformation of alcohols, silyl ethers, and acetals under carbon allylation.

Authors:  Manfred Braun; Wolfgang Kotter
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-16       Impact factor: 15.336

2.  Kinetic resolution of homoaldols via catalytic asymmetric transacetalization.

Authors:  Ilija Čorić; Steffen Müller; Benjamin List
Journal:  J Am Chem Soc       Date:  2010-11-18       Impact factor: 15.419

3.  Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex.

Authors:  Ryo Takita; Kenichiro Yakura; Takashi Ohshima; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2005-10-12       Impact factor: 15.419

4.  Copper-catalyzed coupling of pyridines and quinolines with alkynes: a one-step, asymmetric route to functionalized heterocycles.

Authors:  Daniel A Black; Ramsay E Beveridge; Bruce A Arndtsen
Journal:  J Org Chem       Date:  2008-01-24       Impact factor: 4.354

5.  Catalytic enantioselective aldol-type reaction of beta-ketosters with acetals.

Authors:  Natsuko Umebayashi; Yoshitaka Hamashima; Daisuke Hashizume; Mikiko Sodeoka
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  (S)-(-)-4-[4-[2-(isochroman-1-yl)ethyl]-piperazin-1-yl] benzenesulfonamide, a selective dopamine D4 antagonist.

Authors:  R E TenBrink; C L Bergh; J N Duncan; D W Harris; R M Huff; R A Lahti; C F Lawson; B S Lutzke; I J Martin; S A Rees; S K Schlachter; J C Sih; M W Smith
Journal:  J Med Chem       Date:  1996-06-21       Impact factor: 7.446

7.  Asymmetric spiroacetalization catalysed by confined Brønsted acids.

Authors:  Ilija Čorić; Benjamin List
Journal:  Nature       Date:  2012-03-14       Impact factor: 49.962

8.  Enantioselective addition of terminal alkynes to isolated isoquinoline iminiums.

Authors:  Alexander M Taylor; Stuart L Schreiber
Journal:  Org Lett       Date:  2006-01-05       Impact factor: 6.005

9.  Facile, mild, and highly enantioselective alkynylzinc addition to aromatic aldehydes by BINOL/N-methylimidazole dual catalysis.

Authors:  Fei Yang; Peihua Xi; Li Yang; Jingbo Lan; Rugang Xie; Jingsong You
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

10.  Fam-Ti catalyzed enantioselective alkynylation of aldehydes.

Authors:  Hasan Koyuncu; Ozdemir Dogan
Journal:  Org Lett       Date:  2007-07-24       Impact factor: 6.005
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  1 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
  1 in total

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