☆ 4.7 Article

Diastereoselective Synthesis of Rauhut Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives

JOURNAL OF ORGANIC CHEMISTRY (2017)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 82, 期 1, 页码 781-789

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AMER CHEMICAL SOC

DOI: 10.1021/acs.joc.6b02526

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Chemistry, Organic

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Ministry of Science and Technology of the Republic of China [MOST 103-2113-M-003-009-MY3]

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摘要

A novel, base-catalyzed and highly diastereoselective direct Michael addition-isomerization sequence is presented for the efficient synthesis of Rauhut-Currier-type adducts. An unexpected alpha-addition of gamma-butyroiactam Onto the 3-acyl coumarin derivatives was observed rather thah the gamma-addiction, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent, to those,obtained by, alpha-addition of gamma-butyrolactam onto the corresponding chalcones:

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