Journal ArticleDOI
Organocatalysed asymmetric Mannich reactions.
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
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Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
Journal ArticleDOI
Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
Journal ArticleDOI
Asymmetric Organocatalytic Cyclization and Cycloaddition Reactions
Albert Moyano,Ramon Rios +1 more
Journal ArticleDOI
Recent Developments in Asymmetric Organocatalytic Domino Reactions
TL;DR: The field of asymmetric organocatalytic biomolecular cascades has become one of the most fascinating and current fields in organic chemistry as discussed by the authors, and the literature has been rapidly developing.
References
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Journal ArticleDOI
Enantioselective Mannich Reactions with the Practical Proline Mimetic N-(p-Dodecylphenyl-sulfonyl)-2-pyrrolidinecarboxamide
Hua Yang,Rich G. Carter +1 more
TL;DR: A series of syn-selective Mannich reactions is reported, including the rapid access of alpha- and beta-amino acids surrogates and the use of the industrially attractive nonpolar solvents, such as 2-methyl-tetrahydrofuran.
Journal ArticleDOI
The stereoselective synthesis of α-substituted β-amino secondary alcohols based on the proline-mediated, asymmetric, three-component Mannich reaction and its application to the formal total synthesis of nikkomycins B and Bx
TL;DR: In this paper, a general method for the asymmetric synthesis of α-substituted β-amino secondary alcohols is described, which comprises the four-reaction sequence (1) the proline-mediated, asymmetric, three-component Mannich reaction of two different aldehydes, (2) nucleophilic carbon addition to aldehyde, (3) oxidation of the resulting alcohol to the corresponding ketone, and (4) diastereoselective reduction with LiAlH(O- t -Bu) 3 or catechol
Journal ArticleDOI
Efficient N-p-methoxyphenyl amine deprotection through anodic oxidation.
TL;DR: A new method of deprotection of N-p-methoxyphenylamines using anodic oxidation in acidic medium is presented, which furnishes a high yield of amine and is compatible with several oxidable functional groups.
Journal ArticleDOI
Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines.
TL;DR: This protocol describes a procedure for the synthesis of α, β-branched-b-amino aldehydes via Proline-catalyzed asymmetric Mannich reaction of aldeHydes with N-tert–butoxycarbonyl-imines, formed in good yields and extremely high levels of diastereo- and enantioselectivities.
Journal ArticleDOI
An enantioselective organocatalytic approach to both enantiomers of lasubine II.
Jorge M. M. Verkade,Ferdi van der Pijl,Marian M. J. H. P. Willems,Peter J. L. M. Quaedflieg,Floris L. van Delft,Floris P. J. T. Rutjes +5 more
TL;DR: A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed and the enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction.