Journal ArticleDOI
Organocatalysed asymmetric Mannich reactions.
Reads0
Chats0
TLDR
This tutorial review provides an overview of the recent history of the asymmetric organocatalysed Mannich reaction, including scope and limitations, and application of different catalyst systems.Abstract:
The asymmetric Mannich reaction ranks among the most potent enantioselective and diastereoselective C–C-bond forming reactions. In recent years, organocatalysed versions of asymmetric Mannich processes have been increasingly reported and used in a rapidly growing number of applications. This tutorial review provides an overview of the recent history of the asymmetric organocatalysed Mannich reaction, including scope and limitations, and application of different catalyst systems.read more
Citations
More filters
Journal ArticleDOI
Direct catalytic enantio- and diastereoselective aldol reaction of thioamides.
Mitsutaka Iwata,Ryo Yazaki,I‐Hon Chen,Devarajulu Sureshkumar,Naoya Kumagai,Masakatsu Shibasaki +5 more
TL;DR: A hard Lewis basic phosphine oxide has emerged as an effective additive to constitute a highly active ternary soft Lewis acid/hard Brønsted base/hard Lewis base cooperative catalyst, enabling a direct enantio- and diastereoselective aldol reaction of thiopropionamides.
Journal ArticleDOI
Managing highly coordinative substrates in asymmetric catalysis: a catalytic asymmetric amination with a lanthanum-based ternary catalyst.
TL;DR: The high catalytic performance and enantiocontrol of the reaction with highly coordinative substrates were achieved by the activation/recognition of the substrates exerted by coordination to lanthanum and hydrogen bonding cooperatively in the transition state.
Journal ArticleDOI
Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis.
TL;DR: A chiral Lewis acid/amine base/Brønsted acid combination was used to catalyze a gamma-addition of gamma-butenolides to N-diphenylphosphinoyl imines, affording the products in up to >99% yield, anti/syn = >97:3, and 84% ee.
Journal ArticleDOI
Enantioselective Organocatalyzed Transformations of β-Ketoesters
Thavendran Govender,Per I. Arvidsson,Per I. Arvidsson,Glenn E. M. Maguire,Hendrik G. Kruger,Tricia Naicker +5 more
TL;DR: This review provides comprehensive information on the plethora of organoc atalysts used in stereoselective organocatalyzed construction of β-ketoester-containing compounds.
Journal ArticleDOI
Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides
Lennart Brewitz,Fernando Arteaga Arteaga,Liang Yin,Kaliyamoorthy Alagiri,Naoya Kumagai,Masakatsu Shibasaki +5 more
TL;DR: A comprehensive study on direct and highly stereoselective Mannich-type reactions of α- and β-fluorine-functionalized 7-azaindoline amides that rely on a soft Lewis acid/hard Brønsted base cooperative catalytic system to guarantee an efficient enolization while suppressing undesired defluorination.
References
More filters
Book
Protective groups in organic synthesis
TL;DR: In this article, the most useful groups for the hydroxyl, amino, carboxyl, carbonyl, and sulfhydryl groups are discussed and the chemistry of the classes of these groups, as well as that of individual groups within the class using structures, equations and references.
Journal ArticleDOI
Proline-Catalyzed Direct Asymmetric Aldol Reactions
TL;DR: The finding that the amino acid proline is an effective asymmetric catalyst for the direct aldol reaction between unmodified acetone and a variety of aldehydes is reported.
Book
Greene's Protective Groups in Organic Synthesis
TL;DR: The role of protection groups in organic synthesis is discussed in this paper, where the authors present several general methods for phosphate Ester formation. But none of these methods are suitable for practical applications.
Journal ArticleDOI
Enantioselective Mannich‐Type Reaction Catalyzed by a Chiral Brønsted Acid
Journal ArticleDOI
Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.
Daisuke Uraguchi,Masahiro Terada +1 more
TL;DR: It was found that the phosphoric acid derivatives of general structure 1 serve as highly effective catalysts for the direct addition of acetyl acetone to N-Boc-protected arylimines and functions as an excellent catalyst.