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Sidearm effect: improvement of the enantiomeric excess in the asymmetric Michael addition of indoles to alkylidene malonates
Authors:Zhou Jian  Tang Yong
Affiliation:State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 200032 Shanghai, China.
Abstract:A pseudo-C3-trisoxazoline was designed and synthesized. The improvement of the traditional bisoxazoline into a novel trisoxazoline by a sidearm approach resulted in highly catalytic enantioselective Michael addition of indoles to alkylidene malonates. Excellent catalytic reactivity and enantioselectivity (up to 99% yield and 93% ee) were achieved.
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