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Remote Central‐to‐Axial Chirality Conversion: Direct Atroposelective Ester to Biaryl Transformation
Author(s) -
Link Achim,
Sparr Christof
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201803472
Subject(s) - stereocenter , chirality (physics) , chemistry , silanes , atropisomer , axial chirality , alkoxide , reagent , aryl , combinatorial chemistry , bifunctional , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , alkyl , silane , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
Abstract A strategy for the remote central‐to‐axial chirality conversion by simultaneous planarization of an encoding and a transient stereocenter is presented. Based on a diastereoselective double addition of a chiral 1,5‐bifunctional organomagnesium alkoxide reagent to a broad range of aryl ester substrates, axially chiral biaryls are directly obtained upon in situ reduction. Various structurally distinct atropisomeric biaryl silanes that serve as valuable chiral biaryl anion surrogates are accessible in one step with e.r. values of up to 98:2.