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Stereoselective Alkylation of Allylic Alcohols: Tandem Ethylation and Functionalization
Author(s) -
Das Pragna Pratic,
Lysenko Ivan L.,
Cha Jin Kun
Publication year - 2011
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.201104331
Subject(s) - stereoselectivity , alkylation , electrophile , sn2 reaction , reagent , elaboration , chemistry , allylic rearrangement , tandem , combinatorial chemistry , tsuji–trost reaction , computer science , organic chemistry , philosophy , catalysis , humanities , engineering , aerospace engineering
A versatile formal S N 2′ alkylation of allylic alcohols has been devised by means of the Kulinkovich reagent and in situ elaboration of the presumed alkyltitanium intermediates with electrophiles (see scheme). The utility of this method has been demonstrated in the stereoselective construction of all‐carbon quaternary centers.