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Multi‐Product Classes Obtained from Allylation of α‐Halo Ketones with Allylzinc Bromide
Author(s) -
Zhang Min,
Hu Yuanyuan,
Zhang Songlin
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901487
Subject(s) - bromide , catalysis , allylic rearrangement , trifluoromethanesulfonate , chemistry , ytterbium , organic chemistry , reaction conditions , combinatorial chemistry , materials science , optoelectronics , doping
An efficient, one‐pot synthesis procedure for the preparation of allylic epoxides, aldehydes and homoallylic alcohols (see scheme) has been described. The three industrial products were synthesized by the reaction of allylzinc bromide with α‐halo ketones under non‐catalytic conditions with p ‐toluenesulfonic acid and ytterbium triflate as catalysts, respectively. Feasible reaction mechanisms and intermediates leading to the correlating products are discussed.