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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 
This work was supported by the Japan Society for the Promotion of Science (JSPS), KAKENHI (Grant No. JP19H05630).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2179-5916.
  • Supporting Information


Publication History

Received: 23 June 2023

Accepted after revision: 21 September 2023

Accepted Manuscript online:
21 September 2023

Article published online:
31 October 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
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