Journal ArticleDOI
Organocatalysed asymmetric Mannich reactions.
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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
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B(C6F5)3-Catalyzed C-H Alkylation of N-Alkylamines Using Silicon Enolates without External Oxidant.
TL;DR: An efficient method for the coupling of N-alkylamines with silicon enolates to generate β-amino carbonyl compounds is disclosed and the utility of this method is demonstrated in the late-stage functionalization of bioactive molecules such as citalopram, atomoxetine, and fluoxetines.
Journal ArticleDOI
Brønsted base-catalyzed three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite utilizing [1,2]-phospha-Brook rearrangement.
Azusa Kondoh,Masahiro Terada +1 more
TL;DR: A three-component coupling reaction of α-ketoesters, imines, and diethyl phosphite under Brønsted base catalysis was developed by utilizing the [1,2]-phospha-Brook rearrangement to provide densely functionalized β-amino acid derivatives including an oxygen functionality at the α-position in good yields.
Journal ArticleDOI
Organocatalysed Asymmetric Direct Mannich Reaction of Acetophenone Derivatives and Dibenzo[b,f][1,4]oxazepines with Azetidine‐2‐carboxylic Acid
TL;DR: In this paper, an enantioselective direct Mannich reaction of different acetophenone derivatives with various substituted seven-membered cyclic imines using (S)‐azetidine‐2-carboxylic acid as an organocatalyst is described, which provides an efficient access to optically active 11substituted 10,11−dihydrodibenzo[b,f][1,4]oxazepine derivatives with 87-95
Journal ArticleDOI
Recent synthetic applications of α-amido sulfones as precursors of N-acylimino derivatives
TL;DR: In this article, the most relevant and practical use of α-amido sulfones appeared in the literature after 2005 with particular emphasis on asymmetric synthesis of amino derivatives, and they can be directly used as N-acylimine or Nacyliminium ion precursors in several synthetic processes aimed at the preparation of nitrogen containing compounds.
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Preparation of Conformationally Restricted β2,2- and β2,2,3-Amino Esters and Derivatives Containing an All-Carbon Quaternary Center
TL;DR: The highly challenging preparation of contiguous tertiary and all-carbon quaternary centers was successfully used to generate several β(2,2,3)-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.
References
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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.
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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.