Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes : synthesis of spirocyclic γ-lactams

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

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Bibliographic Details
Main Authors: Lv, Hui, Tiwari, Bhoopendra, Mo, Junming, Xing, Chong, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2013
Online Access:https://hdl.handle.net/10356/97571
http://hdl.handle.net/10220/10587
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Institution: Nanyang Technological University
Language: English
Description
Summary:An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).