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Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions.
Angew Chem Int Ed Engl. 2015 Jul 13; 54(29):8475-9.AC

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhuo CX
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/
Cheng Q
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/
Liu WB
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/
Zhao Q
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/
You SL
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.

MeSH

AlkadienesAllyl CompoundsCatalysisIridiumPyrrolesSpiro CompoundsStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26036866

Citation

Zhuo, Chun-Xiang, et al. "Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives By Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions." Angewandte Chemie (International Ed. in English), vol. 54, no. 29, 2015, pp. 8475-9.
Zhuo CX, Cheng Q, Liu WB, et al. Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions. Angew Chem Int Ed Engl. 2015;54(29):8475-9.
Zhuo, C. X., Cheng, Q., Liu, W. B., Zhao, Q., & You, S. L. (2015). Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions. Angewandte Chemie (International Ed. in English), 54(29), 8475-9. https://doi.org/10.1002/anie.201502259
Zhuo CX, et al. Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives By Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions. Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8475-9. PubMed PMID: 26036866.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Synthesis of Pyrrole-Based Spiro- and Polycyclic Derivatives by Iridium-Catalyzed Asymmetric Allylic Dearomatization and Controllable Migration Reactions. AU - Zhuo,Chun-Xiang, AU - Cheng,Qiang, AU - Liu,Wen-Bo, AU - Zhao,Qiang, AU - You,Shu-Li, Y1 - 2015/06/03/ PY - 2015/03/11/received PY - 2015/05/06/revised PY - 2015/6/4/entrez PY - 2015/6/4/pubmed PY - 2016/1/16/medline KW - asymmetric catalysis KW - dearomatization KW - enantioselectivity KW - iridium KW - stereospecific migration SP - 8475 EP - 9 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 29 N2 - 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. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/26036866/Enantioselective_Synthesis_of_Pyrrole_Based_Spiro__and_Polycyclic_Derivatives_by_Iridium_Catalyzed_Asymmetric_Allylic_Dearomatization_and_Controllable_Migration_Reactions_ DB - PRIME DP - Unbound Medicine ER -