Literature DB >> 18761453

Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation.

Mary P Watson1, Eric N Jacobsen.   

Abstract

The enantioselective, intramolecular arylcyanation of unactivated olefins via C-CN bond activation has been accomplished using a Ni(0) catalyst and BPh3 co-catalyst. High enantioselectivities are achieved using TangPHOS as a chiral ligand. This method allows the generation of two new C-C bonds and one new quaternary carbon stereogenic center in a single synthetic step, converting readily available benzonitrile substrates into 1,1-disubstituted indanes in 49-85% yield and 92-97% ee.

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Year:  2008        PMID： 18761453      PMCID： PMC2596758          DOI： 10.1021/ja805094j

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


  12 in total

1.  Cyanoesterification of 1,2-dienes: synthesis and transformations of highly functionalized alpha-cyanomethylacrylate esters.

Authors:  Yoshiaki Nakao; Yasuhiro Hirata; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2006-06-14       Impact factor: 15.419

2.  A dramatic effect of Lewis-acid catalysts on nickel-catalyzed carbocyanation of alkynes.

Authors:  Yoshiaki Nakao; Akira Yada; Shiro Ebata; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2007-02-13       Impact factor: 15.419

3.  A chiral 1,2-bisphospholane ligand with a novel structural motif: applications in highly enantioselective Rh-catalyzed hydrogenations.

Authors:  Wenjun Tang; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-03       Impact factor: 15.336

4.  Allylcyanation of alkynes: regio- and stereoselective access to functionalized di- or trisubstituted acrylonitriles.

Authors:  Yoshiaki Nakao; Tomoya Yukawa; Yasuhiro Hirata; Shinichi Oda; Jun Satoh; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

5.  Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides.

Authors:  Yusuke Kobayashi; Haruhi Kamisaki; Reiko Yanada; Yoshiji Takemoto
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

6.  Nickel-catalyzed arylcyanation of alkynes.

Authors:  Yoshiaki Nakao; Shinichi Oda; Tamejiro Hiyama
Journal:  J Am Chem Soc       Date:  2004-11-03       Impact factor: 15.419

7.  Enantioselective synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed cyanoamidation.

Authors:  Yoshizumi Yasui; Haruhi Kamisaki; Yoshiji Takemoto
Journal:  Org Lett       Date:  2008-06-27       Impact factor: 6.005

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.  Nickel/BPh3-catalyzed alkynylcyanation of alkynes and 1,2-dienes: an efficient route to highly functionalized conjugated enynes.

Authors:  Yoshiaki Nakao; Yasuhiro Hirata; Masaaki Tanaka; Tamejiro Hiyama
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Asymmetric, catalytic synthesis of alpha-chiral amines using a novel bis(phosphine) monoxide chiral ligand.

Authors:  Alessandro A Boezio; Julien Pytkowicz; Alexandre Côté; André B Charette
Journal:  J Am Chem Soc       Date:  2003-11-26       Impact factor: 15.419
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  13 in total

1.  Palladium catalyzed intramolecular acylcyanation of alkenes using α-iminonitriles.

Authors:  Naveen R Rondla; Jodi M Ogilvie; Zhongda Pan; Christopher J Douglas
Journal:  Chem Commun (Camb)       Date:  2014-08-18       Impact factor: 6.222

2.  Kinetic Resolution via Rh-Catalyzed C-C Activation of Cyclobutanones at Room Temperature.

Authors:  Lin Deng; Yue Fu; Siu Yin Lee; Chengpeng Wang; Peng Liu; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2019-10-02       Impact factor: 15.419

3.  Ni(II) salts and 2-propanol effect catalytic reductive coupling of epoxides and alkynes.

Authors:  Matthew G Beaver; Timothy F Jamison
Journal:  Org Lett       Date:  2011-06-30       Impact factor: 6.005

4.  Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.

Authors:  Grant B Frost; Nicholas A Serratore; Jodi M Ogilvie; Christopher J Douglas
Journal:  J Org Chem       Date:  2017-03-15       Impact factor: 4.354

5.  Transition Metals Catalyzed Element-Cyano Bonds Activations.

Authors:  Rui Wang; John R Falck
Journal:  Catal Rev Sci Eng       Date:  2014-07       Impact factor: 20.217

6.  Enantioselective Nickel-Catalyzed Mizoroki-Heck Cyclizations To Generate Quaternary Stereocenters.

Authors:  Jean-Nicolas Desrosiers; Jialin Wen; Sergei Tcyrulnikov; Soumik Biswas; Bo Qu; Liana Hie; Dmitry Kurouski; Ling Wu; Nelu Grinberg; Nizar Haddad; Carl A Busacca; Nathan K Yee; Jinhua J Song; Neil K Garg; Xumu Zhang; Marisa C Kozlowski; Chris H Senanayake
Journal:  Org Lett       Date:  2017-06-12       Impact factor: 6.005

7.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

8.  Catalytic enantioselective synthesis of indanes by a cation-directed 5-endo-trig cyclization.

Authors:  Craig P Johnston; Abhishek Kothari; Tetiana Sergeieva; Sergiy I Okovytyy; Kelvin E Jackson; Robert S Paton; Martin D Smith
Journal:  Nat Chem       Date:  2015-01-12       Impact factor: 24.427

9.  "Cut and Sew" Transformations via Transition-Metal-Catalyzed Carbon-Carbon Bond Activation.

Authors:  Peng-Hao Chen; Brent A Billett; Tatsuhiro Tsukamoto; Guangbin Dong
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

10.  Transformations of X (C, O, N)-CN Bonds: Cases of Selective X (C, O, N)-C Activation.

Authors:  Rui Wang; John Russell Falck
Journal:  RSC Adv       Date:  2014-01-01       Impact factor: 3.361
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