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. 2023 Jul 17:141:133496.
doi: 10.1016/j.tet.2023.133496. Epub 2023 Jun 13.

Evaluation of helicene-derived 2,2'-bipyridine N- monoxide catalyst for the enantioselective propargylation of N-acylhydrazones with allenyltrichlorosilane

Changgong Xu  1 , Phillip Nader  1 , Jonathan Xavier  1 , Burjor Captain  2 , Norito Takenaka  1
Affiliations

Evaluation of helicene-derived 2,2'-bipyridine N- monoxide catalyst for the enantioselective propargylation of N-acylhydrazones with allenyltrichlorosilane

Changgong Xu et al. Tetrahedron. .

Abstract

Helicene-derived 2,2'-bipyridine N-monoxide was evaluated as a Lewis base catalyst for the enantioselective propargylation of N-acylhydrazones with allenyltrichlorosilane. The helicene-derived catalyst provided moderate-to-good reactivity and enantioselectivity for a range of acylhydrazones. This study represents the first example of the catalytic asymmetric propargylation of non-activated acylhydrazones.

Keywords: Acylhydrazone; Allenyltrichlorosilane; Asymmetric Synthesis; Azahelicene; Organocatalysis.

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Conflict of interest statement

Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Fig. 1.
Fig. 1.
The solid-state structure of 1-aza[6]helicene [14,15]. Its nitrogen atom (blue) is screened by “continuously chiral” framework.
Fig. 2.
Fig. 2.
The solid-state structure of helicene-derived 2,2’-bipyridine N-monoxide catalyst 2 [17] and its expected complex with allenyltrichlorosilane.
Scheme 1.
Scheme 1.
Catalytic enantioselective propargylation of imines.
See this image and copyright information in PMC

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