title: Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions.
abstract: 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.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
authors.forename: Chun-Xiang
authors.initials: CX
authors.lastname: Zhuo
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
authors.forename: Qiang
authors.initials: Q
authors.lastname: Cheng
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
authors.forename: Wen-Bo
authors.initials: WB
authors.lastname: Liu
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhao
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/. slyou@sioc.ac.cn.
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D000466:Alkadienes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000498:Allyl Compounds; D011758:Pyrroles; D013141:Spiro Compounds; C439868:1,5-cyclooctadiene; D007495:Iridium
keywords: asymmetric catalysis; dearomatization; enantioselectivity; iridium; stereospecific migration