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- Title
Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions.
- Authors
Zhuo, Chun ‐ Xiang; Cheng, Qiang; Liu, Wen ‐ Bo; Zhao, Qiang; You, Shu ‐ Li
- Abstract
The first highly diastereo- and enantioselective synthesis of five-membered spiro-2 H-pyrroles was achieved using an Ir-catalyzed asymmetric allylic dearomatization reaction. The spiro-2 H-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.
- Subjects
PYRROLES; CHEMICAL synthesis; IRIDIUM; POLYCYCLIC compounds; MIGRATION reactions (Chemistry); ALLYL compounds
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 29, p8595
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201502259