Bis(2-ethylhexyl)amine as an Effective Organocatalyst for the Racemic Reactions of α,β-Unsaturated Aldehydes Involving an Iminium Ion

Yujiro Hayashi; Xiaolei Han; Naoki Mori

doi:10.1055/a-2179-5916

Synlett, Table of Contents

Synlett 2023; 34(20): 2423-2428
DOI: 10.1055/a-2179-5916

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Special Issue Dedicated to Prof. Hisashi Yamamoto

Bis(2-ethylhexyl)amine as an Effective Organocatalyst for the Racemic Reactions of α,β-Unsaturated Aldehydes Involving an Iminium Ion

Yujiro Hayashi ∗

,

Xiaolei Han

,

Naoki Mori

Abstract

All articles of this category

This letter is dedicated to Prof. Hisashi Yamamoto on the occasion of his 80th birthday.

Abstract

Bis(2-ethylhexyl)amine is shown to be a suitable organocatalyst to prepare racemic compounds in the reactions of α,β-unsaturated aldehydes involving an iminium ion, whereas diphenylprolinol silyl ether is a well-known chiral organocatalyst for the asymmetric versions of the same reactions. The generality and limitations of bis(2-ethylhexyl)amine are disclosed.

Key words

organocatalysis - racemate - diphenylprolinol silyl ether - bis(2-ethylhexyl)amine - α,β-unsaturated aldehyde - iminium ion

Full Text

References

References and Notes

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Supplementary Material

Supporting Information