Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions

The first highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization reaction. The spiro‐2H‐pyrrole derivatives readily undergo a controllable and stereospecific allylic migration under acid catalysis, pro...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-07, Vol.54 (29), p.8475-8479
Main Authors: Zhuo, Chun-Xiang, Cheng, Qiang, Liu, Wen-Bo, Zhao, Qiang, You, Shu-Li
Format: Article
Language:English
Subjects:
Alkadienes - chemistry
Allyl Compounds - chemistry
asymmetric catalysis
Asymmetry
Catalysis
dearomatization
Derivatives
enantioselectivity
iridium
Iridium - chemistry
Migration
Pyrroles
Pyrroles - chemistry
Spiro Compounds - chemistry
Stability
Stereoisomerism
stereospecific migration
Synthesis
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Summary:The first highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization reaction. The spiro‐2H‐pyrrole derivatives readily undergo a controllable and stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values. Additionally, the novel Ir‐complex K1, derived from [Ir(cod)Cl]2 (cod=1,5‐cyclooctadiene) and N‐benzhydryl‐N‐phenyldinaphthophosphoramidite (BHPphos), showed excellent control of both diastereo‐ and enantioselectivities. It's all under control: The highly diastereo‐ and enantioselective synthesis of five‐membered spiro‐2H‐pyrroles was achieved using an Ir‐catalyzed asymmetric allylic dearomatization. The spiro‐2H‐pyrrole derivatives readily undergo a stereospecific allylic migration under acid catalysis, providing polycyclic pyrrole derivatives in excellent yields and ee values.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201502259