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Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

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Abstract

A ferrocene-derived bifunctional phosphine-catalyzed enantioselective [3 + 2] annulation of γ-substituted allenoates with pyrazoloneyldiene oxindoles is investigated for the construction of spiro-cyclopentene-linked oxindole and pyrazolone compounds, which bear three consecutive stereocenters and two vicinal spiroquaternary chiral centers, in good chemical yields (up to 95%) with excellent regio-, diastereo- (dr > 19 : 1) and enantioselectivities (up to 98% ee).

Graphical abstract: Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

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Article information


Submitted
05 Feb 2020
Accepted
18 Mar 2020
First published
19 Mar 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation utilizing a ferrocene derived bifunctional phosphine catalyst

W. Luo, B. Shao, J. Li, X. Xiao, D. Song, F. Ling and W. Zhong, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00140F

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