Highly diastereoselective construction of acyclic systems with two adjacent quaternary stereocenters by allylation of ketones.
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.
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan. takeda-t@cc.tuat.ac.jp
Takeshi
T
Takeda
Masanori
M
Yamamoto
Satoshi
S
Yoshida
Akira
A
Tsubouchi