Literature DB >> 16448108

Axially chiral guanidine as enantioselective base catalyst for 1,4-addition reaction of 1,3-dicarbonyl compounds with conjugated nitroalkenes.

Masahiro Terada1, Hitoshi Ube, Yusuke Yaguchi.   

Abstract

A new strategy for designing chiral guanidine molecules is presented, which features the introduction of an axially chiral binaphthyl backbone. The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity.

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Year:  2006        PMID: 16448108     DOI: 10.1021/ja057848d

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


  13 in total

1.  Arginine mimetics using α-guanidino acids: introduction of functional groups and stereochemistry adjacent to recognition guanidiniums in peptides.

Authors:  Shalini Balakrishnan; Michael J Scheuermann; Neal J Zondlo
Journal:  Chembiochem       Date:  2011-12-23       Impact factor: 3.164

2.  Higher-Order Cyclopropenimine Superbases: Direct Neutral Brønsted Base Catalyzed Michael Reactions with α-Aryl Esters.

Authors:  Eric D Nacsa; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2015-08-04       Impact factor: 15.419

3.  Chiral squaramide derivatives are excellent hydrogen bond donor catalysts.

Authors:  Jeremiah P Malerich; Koji Hagihara; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2008-10-11       Impact factor: 15.419

4.  Catalytic Dynamic Kinetic Resolutions in Tandem to Construct Two-Axis Terphenyl Atropisomers.

Authors:  Omar M Beleh; Edward Miller; F Dean Toste; Scott J Miller
Journal:  J Am Chem Soc       Date:  2020-09-14       Impact factor: 15.419

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.  A solution-phase parallel synthesis of alkylated guanidines from thioisocyanates and amines.

Authors:  Andrey V Bogolubsky; Alexander Grishchenko; Sergey E Pipko; Anzhelika Konovets; Alexander Chuprina; Andrey Tolmachev; Alexander N Boyko; Alexey Chekotylo; Oleg Lukin
Journal:  Mol Divers       Date:  2013-05-01       Impact factor: 2.943

7.  Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters.

Authors:  Jinchao Yang; Alistair J M Farley; Darren J Dixon
Journal:  Chem Sci       Date:  2016-09-14       Impact factor: 9.825

8.  Organocatalytic Michael addition of 1,3-dicarbonyl indane compounds to nitrostyrenes.

Authors:  Zhen-Yu Jiang; Hua-Meng Yang; Ya-Dong Ju; Li Li; Meng-Xian Luo; Guo-Qiao Lai; Jian-Xiong Jiang; Li-Wen Xu
Journal:  Molecules       Date:  2010-04-12       Impact factor: 4.411

9.  Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: application to the ketimine nitro-Mannich reaction.

Authors:  Marta G Núñez; Alistair J M Farley; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

10.  Structure-Activity Relationship Studies of Cyclopropenimines as Enantioselective Brønsted Base Catalysts.

Authors:  Jeffrey S Bandar; Alexandre P Barthelme; Alon Y Mazori; Tristan H Lambert
Journal:  Chem Sci       Date:  2014-12-19       Impact factor: 9.825

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