A catalytic Mannich reaction of a simple ester with no activating functionality at the α-position via a product-base mechanism was reported. The desired Mannich adducts were obtained in high yields using a catalytic amount of KH. This is a rare example of a Brønsted base-catalyzed Mannich reaction of unactivated esters as substrates.

We reported the first enzyme-catalysed, direct, three-component asymmetric Mannich reaction using protease type XIV from Streptomyces griseus (SGP) in acetonitrile. Yields of up to 92% with enantioselectivities of up to 88% e.e. and diastereoselectivities of up to 92:8 (syn:anti) were achieved under the optimised conditions. This enzyme's catalytic promiscuity expands the application of this bi...

Non-coordinated hydroxymethylphosphines react readily with primary and secondary amines by the phosphorus Mannich reaction. To determine if this reactivity can be used to synthesize phosphine macrocycles, trans-Fe(DHMPE)(2)Cl(2) (DHMPE = 1,2-bis(dihydroxymethylphosphino)ethane) was prepared and reacted with various amines. However, no phosphorus Mannich reactivity was observed. In order to unde...

2-Aminoquinolin-4(1H)-one was reacted with various primary/secondary amines and paraformaldehyde under Mannich reaction conditions. In the case of secondary amines, the reaction in N,N-dimethylformamide yielded expected Mannich products accompanied with 3,3'-methylenebis(2-aminoquinolin-4(1H)-one). Except these main products, the pyrimido[4,5-b]quinolin-5-one derivative was also identified as c...

Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-α-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new γ-chloro-α-hydroxy-β-amino esters (dr > 99 : 1). The α-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the ...

Present work describes the synthesis of coumarin Mannich bases 4-7 by the application of Mannich reaction on 7-hydroxy-4-methyl coumarin 3 using conventional as well as microwave technology to compare the feasibility, reaction time and yield of the product. For this, 7-hydroxy-4-methyl coumarin 3 was prepared using Pechmann condensation reaction and Mannich bases (4-7) were synthesized by the r...

The excellent catalytic activity of newly magnetic nanocatalyst FeAl 2 O 4 @PTMS-sulfaguanidine-SA in a one pot multicomponent Mannich-type reaction was used to obtain 2-piperazinyl quinoxaline derivatives with highly selective anti-proliferation efficacy.

The efficient asymmetric synthesis of new chiral γ-chloro-α,β-diamino acid derivatives via highly diastereoselective Mannich-type reactions of N-(diphenylmethylene) glycine esters across a chiral α-chloro-N-p-toluenesulfinylimine was developed. The influence of the base, LDA or LiHMDS, used for the formation of the glycine enolates, was of great importance for the anti-/syn-diastereoselectivity...

A C(1)-symmetric chiral ammonium betaine has been developed, and its intramolecular ion-pairing structure in solid state and its catalytic performance to achieve the highly stereoselective Mannich-type reaction of 2-alkoxythiazol-5(4H)-ones are revealed.

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 rea...