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

被引：0

作者：

Chen, Xi ^{[1
]}

Duan, Zeqing ^{[1
]}

Liu, Min ^{[1
]}

Zheng, Bing ^{[1
]}

Zhang, Qi ^{[2
]}

Guo, Hongchao ^{[1
]}

机构：

[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China

[2] AECC Beijing Inst Aeronaut Mat, AECC Key Lab Adv Corros & Protect Aeronaut Mat, Beijing 100095, Peoples R China

来源：

CHEMISTRYSELECT | 2025年 / 10卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Allenylic alcohol; Annulation; Ketimine; Phosphine; Spirocyclic compound; ASYMMETRIC-SYNTHESIS; CYCLIC IMINES; CHIRAL PHOSPHINES; 4+2 CYCLOADDITION; DOMINO REACTION; DERIVATIVES; ALLENOATES; ALLENES; CARBON; ALKYNES;

D O I：

10.1002/slct.202406016

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The phosphine-catalyzed (3 + 2) annulation reaction of delta-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.

引用

页数：6

共 93 条

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