Literature DB >> 16575932

trans-1-Sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones.

Vicente J Forrat1, Oscar Prieto, Diego J Ramón, Miguel Yus.   

Abstract

The catalytic enantioselective addition of different organozinc reagents (such as alkyl and aryl derivatives or in situ generated aryl, allyl alkenyl, and alkynyl derivatives obtained through different transmetallation processes) to simple ketones has been accomplished by using titanium tetraisopropoxide and chiral ligands derived from substituted trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane, producing the corresponding tertiary alcohols with enantiomeric excesses (ee) up to >99 %. A simple and efficient procedure for the synthesis of the chiral ligands used in these reactions is described.

Entities:  

Year:  2006        PMID: 16575932     DOI: 10.1002/chem.200501397

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  5 in total

1.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

2.  Chiral imine copper chloride-catalyzed enantioselective desymmetrization of 2-substituted 1,2,3-propanetriols.

Authors:  Byunghyuck Jung; Sung Ho Kang
Journal:  Proc Natl Acad Sci U S A       Date:  2007-01-22       Impact factor: 11.205

3.  Palladium-catalysed formation of vicinal all-carbon quaternary centres via propargylation.

Authors:  Xin Huang; Shangze Wu; Wangteng Wu; Pengbin Li; Chunling Fu; Shengming Ma
Journal:  Nat Commun       Date:  2016-08-25       Impact factor: 14.919

4.  Nickel(0)-Catalyzed Decarbonylative Cross-Coupling of Aromatic Esters with Arylboronic Acids via Chelation Assistance.

Authors:  Zhenzhu Hu; Yuhang Wang; Peng Ma; Xiaqian Wu; Jianhui Wang
Journal:  ACS Omega       Date:  2022-06-13

5.  1,2-Addition of Diethylzinc to a Bis(Imidazolyl)ketone Ligand.

Authors:  Emma Folkertsma; Sanne H Benthem; Johann T B H Jastrzebski; Martin Lutz; Marc-Etienne Moret; Robertus J M Klein Gebbink
Journal:  Eur J Inorg Chem       Date:  2018-02-12       Impact factor: 2.524

  5 in total

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