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Highly enantioselective allylic alkylation of 5H-oxazol-4-ones with Morita-Baylis-Hillman carbonates

Author:
Xu, Han, Sha, Feng, Wu, Xin-Yan
Source:
Tetrahedron 2018 v.74 no.32 pp. 4331-4338
ISSN:
0040-4020
Subject:
alkylation, bioactive compounds, carbonates, carboxylic acids, catalytic activity, chemical structure, enantioselectivity
Abstract:
An organocatalytic enantioselective allylic alkylation of 5H-oxazol-4-ones with Morita-Baylis-Hillman carbonates has been developed. With 10 mol% of commercially available cinchonidine, a wide range of substituted 5H-oxazol-4-one derivatives were constructed in good-to-excellent yields with high diastereo- and enantioselectivities. The allylic alkylation adducts obtained are valuable precursors for the synthesis of chiral α-alkyl α-hydroxycarboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.
Agid:
6097606