Issue 11, 2024

Stereodivergent synthesis of chiral spiropyrazolones through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes: unusual solvent effects on the enantioselectivity

Abstract

Chiral spiropyrazolones were constructed for the first time through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes. Through substrate control (by exchanging the position of the double bond and triple bond of 1,3-enyne substrates) and chiral ligand control, four stereoisomers could be obtained with high enantioselectivities. In addition, an interesting solvent effect was observed. The utility of this methodology has been demonstrated by synthesizing a novel type of chiral spiro ligand for enantiodivergent allylation reactions.

Graphical abstract: Stereodivergent synthesis of chiral spiropyrazolones through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes: unusual solvent effects on the enantioselectivity

Supplementary files

Article information

Article type
Research Article
Submitted
25 Feb 2024
Accepted
01 Apr 2024
First published
03 Apr 2024

Org. Chem. Front., 2024,11, 3033-3040

Stereodivergent synthesis of chiral spiropyrazolones through Pd-catalyzed asymmetric sequential hydroalkylation of 1,3-enynes: unusual solvent effects on the enantioselectivity

S. Wang, L. Li, Y. Zheng, L. Li, Y. Wang, F. Peng and Z. Shao, Org. Chem. Front., 2024, 11, 3033 DOI: 10.1039/D4QO00358F

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