Premium
Enantioselective Synthesis of Spiroindenes by Enol‐Directed Rhodium(III)‐Catalyzed CH Functionalization and Spiroannulation
Author(s) -
Reddy Chidipudi Suresh,
Burns David J.,
Khan Imtiaz,
Lam Hon Wai
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201507029
Subject(s) - enantioselective synthesis , rhodium , stereocenter , chemistry , annulation , enol , surface modification , cyclopentadienyl complex , catalysis , enantiomer , isomerization , selectivity , stereochemistry , organic chemistry
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.