Asymmetric Michael addition of aldehydes to nitroalkenes using a primary amino acid lithium salt.
Reads0
Chats0
TLDR
The addition of aldehydes to nitroalkenes was successfully carried out by asymmetric catalysis with L-phenylalanine lithium salt, giving gamma-nitroaldehydes in good yields with high enantioselectivity.Abstract:
Enantioselective Michael addition of aldehydes to nitroalkenes was successfully carried out by asymmetric catalysis with L-phenylalanine lithium salt, giving γ-nitroaldehydes in good yields with high enantioselectivity.read more
Citations
More filters
Journal ArticleDOI
Recent Advances in Metal-Catalyzed Asymmetric 1,4-Conjugate Addition (ACA) of Nonorganometallic Nucleophiles.
TL;DR: This review provides comprehensive and critical information on the enantioselective 1,4-conjugate addition of nonorganometallic (soft) nucleophiles and their importance in synthetic applications.
Journal ArticleDOI
Noncovalent bifunctional organocatalysts: powerful tools for contiguous quaternary-tertiary stereogenic carbon formation, scope, and origin of enantioselectivity.
Thomas C. Nugent,Abdul Sadiq,Ahtaram Bibi,Thomas Heine,Lei Liu Zeonjuk,Nina Vankova,Bassem S. Bassil +6 more
TL;DR: Using racemic α-branched aldehydes, two contiguous (quaternary-tertiary) stereogenic centers can be formed in high diastereo- and enantiomeric excess via an efficient in situ dynamic kinetic resolution, solving a known shortcoming for maleimide electrophiles in particular.
Journal ArticleDOI
Highly Enantioselective Michael Additions of Isobutyraldehyde to Nitroalkenes Promoted by Amphiphilic Bifunctional Primary Amine-Thioureas in Organic or Aqueous Medium
TL;DR: A novel class of chiral amphiphilic bifunctional thioureas based on a beyerane scaffold and each containing a primary amino group were designed and synthesized from the readily available natural product isosteviol and shown to be effective for catalyzing asymmetric Michael additions between isobutyraldehyde and nitroalkenes.
Journal ArticleDOI
Asymmetric organocatalytic functionalization of α,α-disubstituted aldehydes through enamine activation
Journal ArticleDOI
Electrophilicities of trans-β-nitrostyrenes.
Ivo Zenz,Herbert Mayr +1 more
TL;DR: The second-order rate constants for the reactions of trans-β-nitrostyrenes with some enamines were measured and found to agree with those calculated from the electrophilicity parameters E determined in this work and the previously published N and s(N) parameters for enamines.
References
More filters
Journal ArticleDOI
In the Golden Age of Organocatalysis
Peter I. Dalko,Lionel Moisan +1 more
TL;DR: The diverse examples show that in recent years organocatalysis has developed within organic chemistry into its own subdiscipline, whose "Golden Age" has already dawned.
Journal ArticleDOI
The advent and development of organocatalysis
TL;DR: My opinion on why the field of organocatalysis has blossomed so dramatically over the past decade is presented.
Journal ArticleDOI
Diphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes
Journal ArticleDOI
Asymmetric Michael Additions to Nitroalkenes
TL;DR: In this paper, the asymmetric conjugate addition of various carbon and heteroatom nucleophiles to nitroalkenes as a tool for the construction of highly functionalized synthetic building blocks is presented.