Premium
Highly Diastereoselective Construction of Acyclic Systems with Two Adjacent Quaternary Stereocenters by Allylation of Ketones
Author(s) -
Takeda Takeshi,
Yamamoto Masanori,
Yoshida Satoshi,
Tsubouchi Akira
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.201202808
Subject(s) - stereocenter , allylic rearrangement , stereospecificity , chemistry , group (periodic table) , stereochemistry , quaternary carbon , medicinal chemistry , catalysis , organic chemistry , enantioselective synthesis
Unsymmetrical ketones and allyltitanocenes generated by the desulfurizative titanation of γ,γ‐disubstituted allyl phenyl sulfides react under highly diastereoselective construction of adjacent quaternary stereocenters (see scheme; R L =large group, R S =small group). The title reaction is stereospecific: the anti ‐ and syn ‐homoallylic alcohols are obtained by the reaction of E ‐ and Z ‐allylic sulfides, respectively.