Enantioselective β-Selective Addition of Isoxazolidin-5-ones to Allenoates Catalyzed by Quaternary Ammonium Salts

Dedicated to Prof. Cristina Nevado on the occasion of her reception of the 2021 Dr. Margaret Faul Women in Chemistry Award (and thanks for being one of the best friends one can imagine ever since we wrestled with the Iejimalides Cris!!).

Abstract

The enantioselective addition of isoxazolidin-5-ones to the β-carbon of allenoates has been carried out by using a novel spirobiindane-based quaternary ammonium salt catalyst. This protocol, which proceeds under classical liquid-solid phase-transfer conditions, gives access to unprecedented highly functionalized β^2,2-amino acid derivatives with good enantioselectivities and in high yields, and further manipulations of these products have been carried out as well.

Key words

ammonium salt catalysis - organocatalysis - β-amino acids - heterocycles - allenoates

Publication History

Received: 09 August 2022

Accepted: 21 September 2022

Accepted Manuscript online:
21 September 2022

Article published online:
27 October 2022

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