Phosphine-Catalyzed (3 + 2) Annulation of δ-Hydroxyl Allenylic Alcohols with Pyrazolinone-Derived Ketimines

IF 1.9 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

ChemistrySelect Pub Date : 2025-01-22 DOI:10.1002/slct.202406016

Xi Chen, Zeqing Duan, Min Liu, Bing Zheng, Qi Zhang, Hongchao Guo

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引用次数: 0

Abstract

The phosphine-catalyzed (3 + 2) annulation reaction of δ-hydroxyl-substituted allenylic alcohols with pyrazolinone-derived ketimines has been developed, giving a variety of spiro dihydropyrrole-dihydropyrazolone derivatives in high yields with good diastereoselectivities. Various unsaturated pyrazolinone-derived ketimines and diverse allenylic alcohols worked well under mild reaction conditions, 31 examples were provided with up to 97% of yield and >20:1 diastereoselectivity. The scale-up reaction and further transformations of the product were successfully acheived, three derivation experiments showed the feasibility of the annulation product. These results revealed that the current reaction could be a useful tool for the synthesis of spiro dihydropyrrole-dihydropyrazolone derivatives. In addition, we also investigated the asymmetric version of this (3 + 2) annulation of allenylic alcohols with pyrazolinone-derived ketimines, up to 86% ee of chiral product was obtained with the use of chiral bifunctional phosphine catalyst.

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来源期刊

ChemistrySelect Chemistry-General Chemistry

CiteScore

3.30

自引率

4.80%

发文量

1809

审稿时长

1.6 months

期刊介绍： ChemistrySelect is the latest journal from ChemPubSoc Europe and Wiley-VCH. It offers researchers a quality society-owned journal in which to publish their work in all areas of chemistry. Manuscripts are evaluated by active researchers to ensure they add meaningfully to the scientific literature, and those accepted are processed quickly to ensure rapid online publication.