Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation

Reddy?Chidipudi, Suresh; Burns, David J.; Khan, Imtiaz; Lam, Hon Wai

Abstract

Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol?directed C(sp2)?H functionalization and oxidative annulation with alkynes to give spiroindenes containing all?carbon quaternary stereocenters. High selectivity between two possible directing groups, as well as control of the direction of rotation in the isomerization of an O?bound rhodium enolate into the C?bound isomer, appear to be critical for high enantiomeric excesses.

Citation

Reddy Chidipudi, S., Burns, D. J., Khan, I., & Lam, H. W. (2015). Enantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C—H Functionalization and Spiroannulation. Angewandte Chemie International Edition, 54(47), 13975-13979. https://doi.org/10.1002/anie.201507029

• Journal Article Type: Article
• Acceptance Date: Sep 7, 2015
• Online Publication Date: Sep 25, 2015
• Publication Date: Nov 16, 2015
• Deposit Date: Dec 6, 2018
• Publicly Available Date: Feb 5, 2019
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 54
• Issue: 47
• Pages: 13975-13979
• DOI: https://doi.org/10.1002/anie.201507029
• Public URL: https://nottingham-repository.worktribe.com/output/1374068
• Publisher URL: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201507029