Literature DB >> 22777736

Cooperative assistance in bifunctional organocatalysis: enantioselective Mannich reactions with aliphatic and aromatic imines.

Nicolas Probst1, Adám Madarász, Arto Valkonen, Imre Pápai, Kari Rissanen, Antti Neuvonen, Petri M Pihko.   

Abstract

Hold them tight: Guided by X-ray structures, bifunctional thiourea catalysts containing an activating intramolecular hydrogen bond were redesigned. The new catalysts were used to effect a highly enantioselective Mannich reaction between malonates and both aliphatic and aromatic imines (see scheme; Boc=tert-butoxycarbonyl).
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 22777736     DOI： 10.1002/anie.201203852

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

2.  Mechanism-Guided Development of a Highly Active Bis-thiourea Catalyst for Anion-Abstraction Catalysis.

Authors:  C Rose Kennedy; Dan Lehnherr; Naomi S Rajapaksa; David D Ford; Yongho Park; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-10-11       Impact factor: 15.419

3.  Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds.

Authors:  Asia Marie S Riel; Daniel A Decato; Jiyu Sun; Orion B Berryman
Journal:  Chem Commun (Camb)       Date:  2022-01-27       Impact factor: 6.222

4.  Anion-Abstraction Catalysis: The Cooperative Mechanism of α-Chloroether Activation by Dual Hydrogen-Bond Donors.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  ACS Catal       Date:  2016-06-10       Impact factor: 13.084

5.  Torsional and Electronic Factors Control the C-H⋅⋅⋅O Interaction.

Authors:  Russell W Driver; Timothy D W Claridge; Steve Scheiner; Martin D Smith
Journal:  Chemistry       Date:  2016-10-06       Impact factor: 5.236

6.  Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure.

Authors:  Denisa Vargová; Rastislav Baran; Radovan Šebesta
Journal:  Beilstein J Org Chem       Date:  2018-03-05       Impact factor: 2.883

7.  Efficient synthesis of β'-amino-α,β-unsaturated ketones.

Authors:  Isabelle Abrunhosa-Thomas; Aurélie Plas; Nishanth Kandepedu; Pierre Chalard; Yves Troin
Journal:  Beilstein J Org Chem       Date:  2013-03-06       Impact factor: 2.883
  7 in total

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