Literature DB >> 20161177

A Rhodium(I)-Xylyl-BINAP Catalyzed Asymmetric Ynamide-[2 + 2 + 2] Cycloaddition in the Synthesis of Optically Enriched N,O-Biaryls.

Jossian Oppenheimer1, Whitney L Johnson, Ruth Figueroa, Ryuji Hayashi, Richard P Hsung.   

Abstract

A rhodium(I)-xylyl-BINAP catalyzed asymmetric [2 + 2 + 2] cycloaddition of achiral conjugated aryl ynamides with various diynes is described here. This asymmetric cycloaddition provides a series of structurally interesting chiral N,O-biaryls with excellent enantioselectivity along with a modest diastereoselectivity with respect to both C-C and C-N axial chirality.

Entities:  

Year:  2009        PMID： 20161177      PMCID： PMC2724680          DOI： 10.1016/j.tet.2009.03.078

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  67 in total

1.  Transition Metal-Mediated Cycloaddition Reactions.

Authors:  Mark Lautens; Wolfgang Klute; William Tam
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

2.  Rhodium(I)-Catalyzed

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-08       Impact factor: 15.336

3.  Cobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: synthesis of enantiomerically enriched atropoisomers of 2-arylpyridines.

Authors:  Andrey Gutnov; Barbara Heller; Christine Fischer; Hans-Joachim Drexler; Anke Spannenberg; Bernd Sundermann; Corinna Sundermann
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-19       Impact factor: 15.336

4.  Chirality exchange from sp3 central chirality to axial chirality: benzannulation of optically active diaryl-2,2-dichlorocyclopropylmethanols to axially chiral alpha-arylnaphthalenes.

Authors:  Yoshinori Nishii; Kazunori Wakasugi; Keisuke Koga; Yoo Tanabe
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

5.  Nickel-catalyzed highly regioselective multicomponent coupling of ynamides, aldehydes, and silane: a new access to functionalized enamides.

Authors:  Nozomi Saito; Tomoyuki Katayama; Yoshihiro Sato
Journal:  Org Lett       Date:  2008-08-06       Impact factor: 6.005

6.  Application of ynamides in the synthesis of 2-amidoindoles.

Authors:  Karin Dooleweerdt; Thomas Ruhland; Troels Skrydstrup
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

7.  Synthesis of functionalized oxazolones by a sequence of Cu(II)- and Au(I)-catalyzed transformations.

Authors:  Florin M Istrate; Andrea K Buzas; Igor Dias Jurberg; Yann Odabachian; Fabien Gagosz
Journal:  Org Lett       Date:  2008-02-02       Impact factor: 6.005

8.  A sequential metal-catalyzed C-N bond formation in the synthesis of 2-amido-indoles.

Authors:  Pei-Yuan Yao; Yu Zhang; Richard P Hsung; Kang Zhao
Journal:  Org Lett       Date:  2008-08-28       Impact factor: 6.005

9.  Titanium-mediated [2 + 2 + 2] coupling of diynes with homoallylic alcohols.

Authors:  Moo Je Sung; Jin-Hyun Pang; Soon-Bong Park; Jin Kun Cha
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005

10.  A triazole-templated ring-closing metathesis for constructing novel fused and bridged triazoles.

Authors:  Xuejun Zhang; Richard P Hsung; Hongyan Li
Journal:  Chem Commun (Camb)       Date:  2007-06-21       Impact factor: 6.222
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  5 in total

Review 1.  Ynamides: a modern functional group for the new millennium.

Authors:  Kyle A DeKorver; Hongyan Li; Andrew G Lohse; Ryuji Hayashi; Zhenjie Lu; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2010-09-08       Impact factor: 60.622

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  A Stereoselective Intramolecular Cyclopropanation via a De Novo Class of Push-Pull Carbenes Derived from DMDO-Epoxidations of Chiral Ynamides.

Authors:  Hongyan Li; Jennifer E Antoline; Jin-Haek Yang; Ziyad F Al-Rashid; Richard P Hsung
Journal:  New J Chem       Date:  2010-01-01       Impact factor: 3.591

4.  Highly substituted 2-amido-furans from Rh(II)-catalyzed cyclopropenations of ynamides.

Authors:  Hongyan Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

Review 5.  Asymmetric Synthesis of Axially Chiral C-N Atropisomers.

Authors:  Patricia Rodríguez-Salamanca; Rosario Fernández; Valentín Hornillos; José M Lassaletta
Journal:  Chemistry       Date:  2022-03-25       Impact factor: 5.020
  5 in total

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