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Enantioselective Synthesis of 3-Alkyl-1,5-Functionalized 1,4-Diynes via Isoxazol-5(4 H )-ones

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An enantioselective strategy for the synthesis of chiral 3-alkyl-1,5-functionalized 1,4-diynes is reported. The method involves a highly enantioselective organocatalytic conjugate addition of isoxazol-5(4 H )-ones to nitroenynes followed by a Zard-type transformation under one-pot conditions yielding chiral skipped diynes in good overall yields and with excellent enantioselectivities. This study highlights the synthetic versatility of the isoxazol-5(4 H )-one scaffold and its value as a platform for accessing structurally diverse and synthetically relevant building blocks.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04457