scispace - formally typeset
Open AccessJournal ArticleDOI

Asymmetric Michael addition of aldehydes to nitroalkenes using a primary amino acid lithium salt.

Masanori Yoshida, +2 more
- 16 Jun 2010 - 
- Vol. 8, Iss: 13, pp 3031-3036
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

Content maybe subject to copyright    Report

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.

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

Electrophilicities of trans-β-nitrostyrenes.

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

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

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.
Related Papers (5)