The Asymmetric A³(Aldehyde⁻Alkyne⁻Amine) Coupling: Highly Enantioselective Access to Propargylamines.

Jia-Nan Mo,Jiannan Zhao,Junqi Su

doi:10.3390/molecules24071216

Jia-Nan Mo, Jiannan Zhao + Show 1 more

Open Access

https://doi.org/10.3390/molecules24071216

Copy DOI

Abstract

The recent developments in asymmetric A3 (aldehyde–alkyne–amine) coupling has been summarized in this review. Several interesting modifications of the ligands enabled the highly enantioselective synthesis of chiral propargylamines, which are further used in the construction of nitrogen-containing chiral building blocks.

Highlights

Multicomponent reactions (MCRs), defined as one-pot processes in which three or more accessible starting materials are incorporated into a single product without isolating the intermediates, have gained importance in academia and industry [1,2,3,4]
There is no doubt that MCRs are important cornerstones in the diversity-oriented synthesis and combinatorial synthesis compared with stepwise sequential approaches towards complex and important moleculars
By virtue of its inherent advantages, multicomponent reactions have been extensively applied to the total synthesis of complex moleculars and the creation of chemical libraries of drug-like compound [5,6,7]

Summary

Introduction

Multicomponent reactions (MCRs), defined as one-pot processes in which three or more accessible starting materials are incorporated into a single product without isolating the intermediates, have gained importance in academia and industry [1,2,3,4]. PMPNH a All the reactions were performed atmosphere yields were reported as isolated alkynes was improved, probablyunder due an to argon increased steric and hindrance at β-position of the ligand alkynesyield. With the optimal ligand L8, the enantioselectivity of the reactions with PMPNH2 and aliphatic alkynes was improved, probably due to increased steric hindrance at β-position of the ligand. The protocols reported all by Li, Boysen provided direct accesses to a range of optically active propargylamines, all ofSingh themand possess several substrate scope limitations and the three-component reaction with aliphatic remains unsolved. This problem waswas identified by by three-component reaction with aliphatic alkynes remains unsolved. One-pot reaction afforded the corresponding chiral oxazolidinones corresponding chiral oxazolidinones in good yields

AA3 –Coupling Derived from Secondary Amine

13. CuBr-Quinap-catalyzed AA

14. Asymmetric

18. Asymmetric

Findings

Conclusions