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Diastereodivergent aminocatalyzed spirocyclization strategies using 4-alkylideneisoxazol-5-ones and methyl vinyl ketones

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Abstract

Diasterodivergent aminocatalyzed approaches have been developed for the synthesis of racemic 6,10-cis-spiroisoxazol-5-ones and highly enantioenriched 6,10-trans-spiroisoxazol-5-ones, both protocols starting from 4-alkylideneisoxazol-5-ones and methyl vinyl ketones. Reaction monitoring by 1H NMR and HRMS, and DFT calculations have been performed in order to support a mechanistic rationale explaining such outcomes, depending on the reaction conditions employed.

Graphical abstract: Diastereodivergent aminocatalyzed spirocyclization strategies using 4-alkylideneisoxazol-5-ones and methyl vinyl ketones

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Article information


Submitted
30 Jun 2020
Accepted
03 Aug 2020
First published
04 Aug 2020

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

Diastereodivergent aminocatalyzed spirocyclization strategies using 4-alkylideneisoxazol-5-ones and methyl vinyl ketones

A. F. da Silva, I. A. Leonarczyk, M. A. B. Ferreira and I. D. Jurberg, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00779J

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