Bicyclic-guanidine-catalyzed asymmetric Michael addition of 3-substituted oxindoles to 2-cyclopentenone

• Main Authors: Yang, Caiyun, Chen, Wenchao, Yang, Wenguo, Zhu, Bo, Yan, Lin, Tan, Choon-Hong, Jiang, Zhiyong
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Chemistry::Physical chemistry
• Online Access: https://hdl.handle.net/10356/102113; http://hdl.handle.net/10220/18901
• Institution: Nanyang Technological University

Taking the Michael: The first highly enantio- and diastereoselective Michael addition of various 3-benzyl-substituted oxindoles to 2-cyclopentenone has been developed. A variety of 3,3-disubstituted oxindoles as Michael adducts were obtained in 69–99 % yield with 73–98 % ee and 9:1 to >20:1 d.r....