Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions

Enantio- and diastereoselective synthesis of chromeno[4,3-b]pyrrole derivatives bearing tetrasubstituted chirality centers through carbene catalyzed cascade reactions

An NHC-catalyzed cascade cycloaddition reaction is developed for quick access to structurally sophisticated tetrahydrochromeno[4,3-b]pyrrole derivatives. A sterically congested tetrasubstituted chirality carbon center is formed during the cyclization process. All the α-, β-, and carbonyl carbons of...

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Bibliographic Details
Main Authors: Li, Tingting, Wang, Jilan, Xu, Jun, Jin, Jiamiao, Chi, Robin Yonggui, Jin, Zhichao
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2020
Subjects:
Science::Chemistry::Organic chemistry
Chirality
N-Hetereocyclic Carbene
Online Access:https://hdl.handle.net/10356/137900
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Institution: Nanyang Technological University
Language: English
Description
Summary:An NHC-catalyzed cascade cycloaddition reaction is developed for quick access to structurally sophisticated tetrahydrochromeno[4,3-b]pyrrole derivatives. A sterically congested tetrasubstituted chirality carbon center is formed during the cyclization process. All the α-, β-, and carbonyl carbons of the enal substrates are functionalized in chemo- and stereoselective fashion. The multicyclic chromeno[4,3-b]pyrrole products are generally afforded in good yields with excellent enantio- and diastereoselectivities. Heavily substituted pyrroline derivatives can be afforded from the chiral products through simple protocols.

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