Enantioselectivity-Switchable Organocatalytic [4+ 2]-Annulation to Access the Spirooxindole–Norcamphor Scaffold

Release time:2021-07-02

DOI number:10.1021/acs.orglett.0c04164

Journal:Organic Letters

Abstract:An organocatalyzed enantiodivergent synthesis of a multifunctionalized spirooxindole–norcamphor scaffold via a [4 + 2]-annulation between cyclicα, β-unsaturated ketone and methylene indolinones has been established. The presence of CaCl2 in DMF could reverse the enantioselectivity to facilely deliver the enantiomers of the corresponding spirooxindoles. Both enantiomers of the corresponding spirooxindoles were obtained in excellent yield and diastereo-/enantioselectivity by employing one single prolinosulfonamide catalyst.

Co-author:Xian-Zhou Zheng, Jun-An Xiao, Hao-Yue Xiang

First Author:Jing Wan

Indexed by:Journal paper

Correspondence Author:Kai Chen*, Xiao-Qing Chen*, Hua Yang*

Volume:23

Issue:3

Page Number:963-968

Translation or Not:no

Date of Publication:2021-01-22

Links to published journals:https://pubs.acs.org/doi/abs/10.1021/acs.orglett.0c04164