Intramolecular Mannich Reaction in the Asymmetric Synthesis of Polysubstituted Piperidines:  Concise Synthesis of the Dendrobate Alkaloid (+)-241D and Its C-4 Epimer

2001 ◽  
Vol 3 (20) ◽  
pp. 3169-3171 ◽  
Author(s):  
Franklin A. Davis ◽  
Bin Chao ◽  
Ashwin Rao
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Polysubstituted Piperidines

Carbonyl catalysis enables a biomimetic asymmetric Mannich reaction

Science ◽  
2018 ◽  
Vol 360 (6396) ◽  
pp. 1438-1442 ◽  
Author(s):  
Jianfeng Chen ◽  
Xing Gong ◽  
Jianyu Li ◽  
Yingkun Li ◽  
Jiguo Ma ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
High Activity ◽  
Asymmetric Catalysis ◽  
Carbonyl Group ◽  
Mannich Reaction ◽  
Primary Amine ◽  
Chiral Amines ◽  
Carbonyl Groups ◽  
Diphenylphosphinyl Imines

Chiral amines are widely used as catalysts in asymmetric synthesis to activate carbonyl groups for α-functionalization. Carbonyl catalysis reverses that strategy by using a carbonyl group to activate a primary amine. Inspired by biological carbonyl catalysis, which is exemplified by reactions of pyridoxal-dependent enzymes, we developed an N-quaternized pyridoxal catalyst for the asymmetric Mannich reaction of glycinate with aryl N-diphenylphosphinyl imines. The catalyst exhibits high activity and stereoselectivity, likely enabled by enzyme-like cooperative bifunctional activation of the substrates. Our work demonstrates the catalytic utility of the pyridoxal moiety in asymmetric catalysis.

Asymmetric Synthesis of 2,3,6-Trisubstituted Piperidines via Baylis–Hillman Adducts and Lithium Amide through Domino Reaction

Synlett ◽  
2019 ◽  
Vol 31 (06) ◽  
pp. 600-604 ◽  
Author(s):  
Mateo M. Salgado ◽  
Alejandro Manchado ◽  
Carlos T. Nieto ◽  
David Díez ◽  
Narciso M. Garrido
Keyword(s):  
Amino Acid ◽  
Asymmetric Synthesis ◽  
Claisen Rearrangement ◽  
Domino Reaction ◽  
Amino Acid Derivative ◽  
Side Chain ◽  
Lithium Amide ◽  
Stereochemical Control ◽  
Asymmetric Michael Addition ◽  
Polysubstituted Piperidines

A convenient asymmetric synthesis of methyl (2S,3S,6R)-6-(4-fluorophenyl)-2-(4-hydroxyphenyl)-piperidine-3-carboxylate is described, starting from Baylis–Hillman adducts. The route involves a domino process: allylic acetate rearrangement, stereoselective Ireland–Claisen rearrangement and asymmetric Michael addition, which provides a δ-amino acid derivative with full stereochemical control. A subsequent chemoselective transformation of one of the side-chain groups allows an effective cyclization leading to biologically interesting polysubstituted piperidines in which the 2,6-aryl groups could be attached sequentially.

scholarly journals Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study

RSC Advances ◽  
2016 ◽  
Vol 6 (38) ◽  
pp. 31861-31870 ◽  
Author(s):  
Amedeo Capobianco ◽  
Antonia Di Mola ◽  
Valentina Intintoli ◽  
Antonio Massa ◽  
Vito Capaccio ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Phase Transfer Catalysis ◽  
Theoretical Study ◽  
Phase Transfer ◽  
Chiral Phase

The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of amines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC).

Asymmetric synthesis of (−)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones

2018 ◽  
Vol 16 (5) ◽  
pp. 771-779 ◽  
Author(s):  
Yi-Wen Liu ◽  
Rui-Jun Ma ◽  
Jia-Hang Yan ◽  
Zhu Zhou ◽  
Bang-Guo Wei
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction

An approach to access the 3-hydroxyl-2,6-disubstituted piperidine scaffold has been developed through the Mannich process involving N,O-acetals and ketones, and the process is demonstrated by the asymmetric synthesis of (−)-sedacryptine.

A general approach for the asymmetric synthesis of densely substituted piperidines and fully substituted piperidinones employing the asymmetric Mannich reaction as key step

RSC Advances ◽  
2013 ◽  
Vol 3 (48) ◽  
pp. 25800 ◽  
Author(s):  
Ainara Iza ◽  
Uxue Uria ◽  
Efraím Reyes ◽  
Luisa Carrillo ◽  
Jose L. Vicario
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction

scholarly journals Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction

2017 ◽  
Vol 82 (13) ◽  
pp. 7050-7058 ◽  
Author(s):  
Pankaj Chauhan ◽  
Suruchi Mahajan ◽  
Uğur Kaya ◽  
Anssi Peuronen ◽  
Kari Rissanen ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Mannich Reaction ◽  
Pyrazolone Derivatives
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