Literature DB >> 12785777

Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition.

Do Hyun Ryu1, E J Corey.   

Abstract

The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.

Entities:  

Year:  2003        PMID： 12785777     DOI： 10.1021/ja035393r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective.

Authors:  Timothy S De Vries; Aleksandrs Prokofjevs; Edwin Vedejs
Journal:  Chem Rev       Date:  2012-04-20       Impact factor: 60.622

2.  Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors:  Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-20       Impact factor: 15.336

3.  Asymmetric Synthesis of Griffipavixanthone Employing a Chiral Phosphoric Acid-Catalyzed Cycloaddition.

Authors:  Michael J Smith; Kyle D Reichl; Randolph A Escobar; Thomas J Heavey; David F Coker; Scott E Schaus; John A Porco
Journal:  J Am Chem Soc       Date:  2018-12-26       Impact factor: 15.419

4.  Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

Authors:  Xiao-Hui Yang; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-08-09       Impact factor: 15.419

5.  Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

6.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

7.  Total Synthesis of (-)-Nahuoic Acid Ci (Bii).

Authors:  Qi Liu; Yifan Deng; Amos B Smith
Journal:  J Am Chem Soc       Date:  2017-09-21       Impact factor: 15.419

8.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205

9.  Superelectrophilic intermediates in nitrogen-directed aromatic borylation.

Authors:  Timothy S De Vries; Aleksandrs Prokofjevs; Jeremy N Harvey; Edwin Vedejs
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

10.  Efficient Synthesis of the Cyclopentanone Fragrances (Z)-3-(2-oxopropyl)-2-(pent-2-en-1-yl)cyclopentanone and Magnolione.

Authors:  Guojun Pan; Robert M Williams
Journal:  Tetrahedron       Date:  2014-01-14       Impact factor: 2.457
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