Chiral Phosphoric Acid Catalyzed Cascade Asymmetric Allylboration/Oxa-Cyclization of Aldehydes for Access to Multisubstituted Tetrahydrofurans

Abstract

Optically pure homoallylic alcohols, important synthons for natural products and bioactive compounds, can be assembled by a chiral phosphoric acid catalyzed asymmetric allylboration of aldehydes. Based on this reaction, two unprecedented cascade reactions of functionalized aldehydes (allylation/oxa-Michael or oxa-Pictet–Spengler reactions) for the synthesis of chiral 2,5-disubstituted and 2,2,5-trisubstituted tetrahydrofurans using a single chiral phosphoric acid catalyst have been developed. The reaction mechanism proposed here of the oxa-Pictet–Spengler reaction was investigated through control experiments.

Key words

substituted tetrahydrofurans - chiral phosphoric acid - cascade reaction - allylboration - oxa-cyclization

Publication History

Received: 15 December 2024

Accepted after revision: 09 January 2025

Accepted Manuscript online:
09 January 2025

Article published online:
20 February 2025

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