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

Angew Chem Int Ed Engl

School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK) http://www.nottingham.ac.uk/∼pczhl.

Published: November 2015

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Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol-directed C(sp(2))-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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648053PMC
http://dx.doi.org/10.1002/anie.201507029DOI Listing

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