Literature DB >> 23321009

Enantioselective formal aza-Diels-Alder reactions of enones with cyclic imines catalyzed by primary aminothioureas.

Mathieu P Lalonde1, Meredeth A McGowan, Naomi S Rajapaksa, Eric N Jacobsen.   

Abstract

A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

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Year:  2013        PMID： 23321009      PMCID： PMC3566267          DOI： 10.1021/ja310718f

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


  31 in total

1.  Structure-based analysis and optimization of a highly enantioselective catalyst for the strecker reaction.

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

2.  Cooperative coexistence: effective interplay of two Brønsted acids in the asymmetric synthesis of isoquinuclidines.

Authors:  Magnus Rueping; Cengiz Azap
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-27       Impact factor: 15.336

3.  Enantioselective Pictet-Spengler-type cyclizations of hydroxylactams: H-bond donor catalysis by anion binding.

Authors:  Izzat T Raheem; Parvinder S Thiara; Emily A Peterson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2007-10-17       Impact factor: 15.419

Review 4.  (Thio)urea organocatalysis--what can be learnt from anion recognition?

Authors:  Zhiguo Zhang; Peter R Schreiner
Journal:  Chem Soc Rev       Date:  2009-02-18       Impact factor: 54.564

5.  Direct catalytic asymmetric synthesis of anti-1,2-amino alcohols and syn-1,2-diols through organocatalytic anti-Mannich and syn-aldol reactions.

Authors:  S S V Ramasastry; Haile Zhang; Fujie Tanaka; Carlos F Barbas
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

6.  Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

Authors:  Noah Z Burns; Michael R Witten; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2011-08-25       Impact factor: 15.419

7.  Synthesis and stereochemistry of 7-phenyl-2-propionanilidobenzo[a]quinolizidine derivatives. Structural probes of fentanyl analgesics.

Authors:  B E Maryanoff; D F McComsey; R J Taylor; J F Gardocki
Journal:  J Med Chem       Date:  1981-01       Impact factor: 7.446

8.  Highly enantioselective addition of ketones to nitroolefins catalyzed by new thiourea-amine bifunctional organocatalysts.

Authors:  Svetlana B Tsogoeva; Shengwei Wei
Journal:  Chem Commun (Camb)       Date:  2006-02-23       Impact factor: 6.222

9.  Cooperative catalysis by tertiary amino-thioureas: mechanism and basis for enantioselectivity of ketone cyanosilylation.

Authors:  Stephan J Zuend; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2007-12-05       Impact factor: 15.419

10.  Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones.

Authors:  Giuseppe Bartoli; Marcella Bosco; Armando Carlone; Fabio Pesciaioli; Letizia Sambri; Paolo Melchiorre
Journal:  Org Lett       Date:  2007-03-09       Impact factor: 6.005
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  13 in total

1.  Chiral Thioureas Promote Enantioselective Pictet-Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction.

Authors:  Rebekka S Klausen; C Rose Kennedy; Alan M Hyde; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419

2.  A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.

Authors:  Hua-Li Qin; Qinheng Zheng; Grant A L Bare; Peng Wu; K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

3.  A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.

Authors:  Michael R Witten; Eric N Jacobsen
Journal:  Org Lett       Date:  2015-05-08       Impact factor: 6.005

4.  Enantioselective Syntheses of Yohimbine Alkaloids: Proving Grounds for New Catalytic Transformations.

Authors:  Eric R Miller; Karl A Scheidt
Journal:  Synthesis (Stuttg)       Date:  2021-11-02       Impact factor: 2.969

5.  Rhodium-catalyzed asymmetric hydrogenation of unprotected NH imines assisted by a thiourea.

Authors:  Qingyang Zhao; Jialin Wen; Renchang Tan; Kexuan Huang; Pedro Metola; Rui Wang; Eric V Anslyn; Xumu Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-18       Impact factor: 15.336

6.  Enantioselective total synthesis of (+)-reserpine.

Authors:  Naomi S Rajapaksa; Meredeth A McGowan; Matthew Rienzo; Eric N Jacobsen
Journal:  Org Lett       Date:  2013-01-18       Impact factor: 6.005

7.  Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes.

Authors:  Xiaoxiao Song; Qijian Ni; Chen Zhu; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-11-06       Impact factor: 3.157

Review 8.  (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers.

Authors:  Giorgos Koutoulogenis; Nikolaos Kaplaneris; Christoforos G Kokotos
Journal:  Beilstein J Org Chem       Date:  2016-03-10       Impact factor: 2.883

9.  Strong Brønsted acid promoted asymmetric hydrogenation of isoquinolines and quinolines catalyzed by a Rh-thiourea chiral phosphine complex via anion binding.

Authors:  Jialin Wen; Renchang Tan; Shaodong Liu; Qingyang Zhao; Xumu Zhang
Journal:  Chem Sci       Date:  2016-01-26       Impact factor: 9.825

10.  Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.

Authors:  Xiang Wu; Shi-Bao Zhao; Lang-Lang Zheng; You-Gui Li
Journal:  Molecules       Date:  2018-09-01       Impact factor: 4.411
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