Literature DB >> 15969569

Thiourea-catalyzed enantioselective cyanosilylation of ketones.

Douglas E Fuerst1, Eric N Jacobsen.   

Abstract

The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a cooperative mechanism involving electrophile activation by thiourea and nucleophile activation by the amine.

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Year:  2005        PMID： 15969569      PMCID： PMC3166885          DOI： 10.1021/ja052511x

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


  28 in total

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Authors:  Petr Vachal; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2002-08-28       Impact factor: 15.419

2.  Highly enantioselective catalytic acyl-pictet-spengler reactions.

Authors:  Mark S Taylor; Eric N Jacobsen
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3.  Highly enantioselective thiourea-catalyzed nitro-Mannich reactions.

Authors:  Tehshik P Yoon; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

4.  Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts.

Authors:  Albrecht Berkessel; Felix Cleemann; Santanu Mukherjee; Thomas N Müller; Johann Lex
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

5.  Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

Authors:  Benedek Vakulya; Szilárd Varga; Antal Csámpai; Tibor Soós
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

6.  Second-generation organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones.

Authors:  Albrecht Berkessel; Santanu Mukherjee; Felix Cleemann; Thomas N Muller; Johann Lex
Journal:  Chem Commun (Camb)       Date:  2005-02-15       Impact factor: 6.222

7.  Enantioselective cyanosilylation of ketones catalyzed by a chiral oxazaborolidinium ion.

Authors:  Do Hyun Ryu; E J Corey
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

8.  Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quaternary amino acids.

Authors:  P Vachal; E N Jacobsen
Journal:  Org Lett       Date:  2000-03-23       Impact factor: 6.005

9.  Metal-free organocatalysis through explicit hydrogen bonding interactions.

Authors:  Peter R Schreiner
Journal:  Chem Soc Rev       Date:  2003-09       Impact factor: 54.564

10.  Enantioselective aza-Henry reaction catalyzed by a bifunctional organocatalyst.

Authors:  Tomotaka Okino; Satoru Nakamura; Tomihiro Furukawa; Yoshiji Takemoto
Journal:  Org Lett       Date:  2004-02-19       Impact factor: 6.005
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  13 in total

1.  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

2.  Toward a practical and waste-free synthesis of thioureas in water.

Authors:  Najmedin Azizi; Alireza Khajeh-Amiri; Hossein Ghafuri; Mohammad Bolourtchian
Journal:  Mol Divers       Date:  2010-02-24       Impact factor: 2.943

Review 3.  Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors:  Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
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4.  Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

Authors:  Dustin S Siegel; Grazia Piizzi; Giovanni Piersanti; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2009-12-18       Impact factor: 4.354

5.  Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

Authors:  Patrick G McGarraugh; Stacey E Brenner
Journal:  Tetrahedron       Date:  2009-01-10       Impact factor: 2.457

6.  Effect of carbonates/phosphates as nucleophilic catalysts in dimethylformamide for efficient cyanosilylation of aldehydes and ketones.

Authors:  G K Surya Prakash; Habiba Vaghoo; Chiradeep Panja; Vijayalakshmi Surampudi; Roman Kultyshev; Thomas Mathew; George A Olah
Journal:  Proc Natl Acad Sci U S A       Date:  2007-02-22       Impact factor: 11.205

7.  Synthesis and evaluation of new guanidine-thiourea organocatalyst for the nitro-Michael reaction: Theoretical studies on mechanism and enantioselectivity.

Authors:  Tatyana E Shubina; Matthias Freund; Sebastian Schenker; Timothy Clark; Svetlana B Tsogoeva
Journal:  Beilstein J Org Chem       Date:  2012-09-07       Impact factor: 2.883

Review 8.  Chiral poly-rare earth metal complexes in asymmetric catalysis.

Authors:  Masakatsu Shibasaki
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2006-04       Impact factor: 3.493

9.  Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes.

Authors:  Zhipeng Zhang; Han Yong Bae; Joyram Guin; Constantinos Rabalakos; Manuel van Gemmeren; Markus Leutzsch; Martin Klussmann; Benjamin List
Journal:  Nat Commun       Date:  2016-08-17       Impact factor: 14.919

10.  Organocatalytic enantio- and diastereoselective cycloetherification via dynamic kinetic resolution of chiral cyanohydrins.

Authors:  Naoki Yoneda; Yuki Fujii; Akira Matsumoto; Keisuke Asano; Seijiro Matsubara
Journal:  Nat Commun       Date:  2017-11-09       Impact factor: 14.919
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