%0 Journal Article
%T Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers
%A Abigail Page
%A Jonathan Clayden
%J Beilstein Journal of Organic Chemistry
%D 2011
%I 
%R 10.3762/bjoc.7.156
%X Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi¨C( )-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r.
%K configurational stability
%K diaryl ether
%K diastereoselective
%K enantioselective
%K lateral lithiation
%K metallation
%U http://dx.doi.org/10.3762/bjoc.7.156