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Issue 20, 2020
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Enantioselective synthesis of indanone spiro-isochromanone derivatives via a dinuclear zinc-catalyzed Michael/transesterification tandem reaction

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Abstract

An enantioselective Michael/transesterification tandem reaction of α-hydroxy indanones with ortho-ester chalcones was realized using dinuclear zinc catalysts. A series of enantiomerically pure spiro[indanone-2,3′-isochromane-1-one] derivatives were obtained in good yields with excellent stereoselectivities (up to >20 : 1 dr, up to >99% ee). This protocol could be conducted on a gram scale without affecting its stereoselectivities. In addition, the absolute stereochemistry of the products was determined by X-ray crystallographic analysis of 3ac, and a positive nonlinear effect was observed. Finally, a possible catalytic cycle was proposed to explain the origin of the enantioselectivity.

Graphical abstract: Enantioselective synthesis of indanone spiro-isochromanone derivatives via a dinuclear zinc-catalyzed Michael/transesterification tandem reaction

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Article information


Submitted
13 Mar 2020
Accepted
04 May 2020
First published
05 May 2020

Org. Biomol. Chem., 2020,18, 3917-3926
Article type
Paper

Enantioselective synthesis of indanone spiro-isochromanone derivatives via a dinuclear zinc-catalyzed Michael/transesterification tandem reaction

X. Yang, M. Xu, J. Wang, M. Liu, F. Mathey, Y. Hua and M. Wang, Org. Biomol. Chem., 2020, 18, 3917
DOI: 10.1039/D0OB00541J

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