Literature DB >> 17555361

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

Fei Yang1, Peihua Xi, Li Yang, Jingbo Lan, Rugang Xie, Jingsong You.   

Abstract

The dual Lewis acid/base catalytic system, generated from N-methylimidazole (NMI), (R)-1,1'-bi-2-naphthol [(R)-BINOL], and Ti(OiPr)4, effectively catalyzes the enantioselective alkynylation of aldehydes in the presence of Et2Zn in good yields and excellent enantioselectivities of up to 94% ee at room temperature. The mild reaction conditions make it possible to use functional alkynes in this asymmetric addition.

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Year:  2007        PMID: 17555361     DOI: 10.1021/jo0707535

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

1.  Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.

Authors:  Harathi D Srinivas; Prantik Maity; Glenn P A Yap; Mary P Watson
Journal:  J Org Chem       Date:  2015-04-07       Impact factor: 4.354

2.  Copper-catalyzed enantioselective additions to oxocarbenium ions: alkynylation of isochroman acetals.

Authors:  Prantik Maity; Harathi D Srinivas; Mary P Watson
Journal:  J Am Chem Soc       Date:  2011-10-11       Impact factor: 15.419

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

Authors:  Mary P Watson; Prantik Maity
Journal:  Synlett       Date:  2012       Impact factor: 2.454

4.  Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Org Lett       Date:  2012-02-22       Impact factor: 6.005

5.  Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.

Authors:  Barry M Trost; Mark J Bartlett; Andrew H Weiss; Axel Jacobi von Wangelin; Vincent S Chan
Journal:  Chemistry       Date:  2012-10-23       Impact factor: 5.236

6.  Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

Authors:  Barry M Trost; Alicia C Gutierrez; Robert C Livingston
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

7.  Continuous-flow hydration-condensation reaction: Synthesis of α,β-unsaturated ketones from alkynes and aldehydes by using a heterogeneous solid acid catalyst.

Authors:  Magnus Rueping; Teerawut Bootwicha; Hannah Baars; Erli Sugiono
Journal:  Beilstein J Org Chem       Date:  2011-12-15       Impact factor: 2.883

8.  Zinc mediated azide-alkyne ligation to 1,5- and 1,4,5-substituted 1,2,3-triazoles.

Authors:  Christopher D Smith; Michael F Greaney
Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

Review 9.  Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions.

Authors:  Jixin Liu; Srimoyee Dasgupta; Mary P Watson
Journal:  Beilstein J Org Chem       Date:  2015-12-22       Impact factor: 2.883

10.  A General Asymmetric Synthesis of (R)-Matsutakeol and Flavored Analogs.

Authors:  Jia Liu; Honglian Li; Chao Zheng; Shichao Lu; Xianru Guo; Xinming Yin; Risong Na; Bin Yu; Min Wang
Journal:  Molecules       Date:  2017-02-27       Impact factor: 4.411

  10 in total

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