☆ 4.8 Article

Organocatalytic Asymmetric Michael Addition of 5H-Oxazol-4-ones to Nitroolefins

ORGANIC LETTERS (2013)

期刊

ORGANIC LETTERS

卷 15, 期 10, 页码 2358-2361

出版社

AMER CHEMICAL SOC

DOI: 10.1021/ol401062z

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Chemistry, Organic

资金

NSFC [21072044, 21202034]
Program for New Century Excellent Talents in University of Ministry of Education [NCET-11-0938]
Excellent Youth Foundation of Henan Scientific Committee [114100510003]

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摘要

The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral alpha-alkyl-alpha-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.

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