TY - JOUR
T1 - Diastereoselective Synthesis of Rauhut-Currier-Type Adducts via an Unexpected α-Addition of α,β-Unsaturated γ-Butyrolactams to Coumarin Derivatives
AU - Yang, Shu Mei
AU - Madhusudhan Reddy, Ganapuram
AU - Liu, Meng Hsien
AU - Wang, Tzu Ping
AU - Yu, Jhen Kuei
AU - Lin, Wenwei
PY - 2017/1/6
Y1 - 2017/1/6
N2 - 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.
AB - 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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U2 - 10.1021/acs.joc.6b02526
DO - 10.1021/acs.joc.6b02526
M3 - Article
C2 - 27936710
AN - SCOPUS:85018506638
VL - 82
SP - 781
EP - 789
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -