Premium
Stereoarrays with an All‐Carbon Quaternary Center: Diastereoselective Desymmetrization of Prochiral Malonaldehydes
Author(s) -
Linclau Bruno,
Cini Elena,
Oakes Catherine S.,
Josse Solen,
Light Mark,
Ironmonger Victoria
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107370
Subject(s) - stereocenter , stannane , desymmetrization , nucleophile , chemistry , center (category theory) , chelation , stereochemistry , combinatorial chemistry , computer science , organic chemistry , enantioselective synthesis , catalysis , crystallography
Tamed by chelation : The MgBr 2 chelation of prochiral malonaldehydes allows diastereoselective monoaddition reactions with allyl stannane nucleophiles (see scheme; PG=protecting group, TBDMS= tert ‐butyldiphenylmethylsilyl, Tr=trityl). In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all‐carbon quaternary center.