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Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated
Shu-Mei Yang1, Ganapuram Madhusudhan Reddy1, Meng-Hsien Liu1
1Department of Chemistry, National Taiwan Normal University , 88, Sec. 4, Tingchow Road, Taipei 11677, Taiwan R.O.C.
Abstract:
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 α-addition of γ-butyrolactam onto the 3-acyl coumarin derivatives was observed rather than the γ-addition, which is more common. The adducts could further undergo hydrolysis/decarboxylation to generate the products which are equivalent to those obtained by α-addition of γ-butyrolactam onto the corresponding chalcones.
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