Simple preparation of chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) and applications to asymmetric alkylative esterification

doi:10.1016/S0957-4166(98)00152-9

Paper

Simple preparation of chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) and applications to asymmetric alkylative esterification

Published May 22, 1998 · T. Isobe, Keiko Fukuda, T. Ishikawa

Tetrahedron-asymmetry

UNKNOWN SJR score

37

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1

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Abstract

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Study Snapshot

Chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) can be easily prepared and applied to asymmetric alkylative esterification of benzoic acid with (1-bromoethyl)benzene.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Simple preparation of chiral 1,3-dimethyl-2-iminoimidazolidines (monocyclic guanidines) and applications to asymmetric alkylative esterification

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References

Enantiomerically pure guanidine-catalysed asymmetric nitroaldol reaction

Enantiomerically pure guanidines can catalyze the asymmetric nitroaldol reaction, with enantioselectivity influenced by the structure, amount, solvent, and temperature.

Studies directed toward the design of chiral acylating agents. The utility of chiral N-benzoylimides in enantioselective alcohol acylation

N-benzoyl-4(S)-tert-butyl-2-oxazolidinone (1b) is an efficient enantioselective acylating agent for aryl n-alkyl carbinols, with kinetic selectivities of 20-30

Synthesis and properties of a series of sterically hindered guanidine bases

These sterically hindered guanidine bases are easy to prepare and show potential for use in organic synthesis due to their resistance to alkylating agents.

A Convenient Procedure for Esterification of Carboxylic Acids

This simple reaction provides a general method for esterifying various carboxylic acids, yielding esters in good yields in various conditions.

Citations

The Enantiopure 1,2-Diphenylethylenediamine (DPEDA) Motif in the Development of Organocatalysts for Asymmetric Reactions: Advances in the Last 20 Years

DPEDA-based organocatalysts have made significant advances in enantioselective organic reactions, providing valuable information on reaction mechanisms and bi/multifunctional structures.

Recent strategies and tactics for the enantioselective total syntheses of cyclolignan natural products.

Recent strategies for enantioselective total syntheses of cyclolignan natural products have shown promise for their potential use in traditional and conventional medicine.

Chiral organobases: Properties and applications in asymmetric catalysis

Chiral organobases, such as tertiary amines and amidines, are effective organocatalysts for various base-initiated reactions with excellent yields and stereoselectivities.

Synthesis, structure, and reaction of chiral 2-azidoimidazolinium salts: (7aS)-3-azido-5,6,7,7a-tetrahydro-2-[(1R)-1-phenylethyl]-1H-pyrrolo[1,2-c]imidazolium hexafluorophosphate and 2-azido-1,3-bis[(S)-1-phenylethyl]imidazolinium hexafluorophosphate

Chiral 2-azidoimidazolinium salts were synthesized and characterized, but their migration amidation reaction with enol silyl ether showed poor diastereoselectivity.

Design and synthesis of a chiral seven-membered ring guanidine organocatalyst applied to asymmetric vinylogous aldol reactions

The chiral seven-membered ring guanidine organocatalyst effectively forms optically active -butenolide products in asymmetric vinylogous aldol reactions with dr's and er's up to 90:10 and 97:3.