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Synthesis of Enantiopure Homoallylic Alcohols
Author(s) -
Tietze Lutz F.,
Schiemann Kai,
Wegner Christoph,
Wulff Christian
Publication year - 1998
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/(sici)1521-3765(19980904)4:9<1862::aid-chem1862>3.0.co;2-c
Subject(s) - enantiopure drug , ketone , ether , chemistry , organic chemistry , catalysis , trimethylsilyl , selectivity , mixing (physics) , enantioselective synthesis , physics , quantum mechanics
The faciall‐selective allylation of aliphatic ketones is a so far unsolved problem . Here a new method is presented which gives a 24:1 selectivity even for ethyl methyl ketone. The reaction proceeds in a domino‐type fashion from mixing of the ketone 1 , a chiral trimethylsilyl ether 2 derived from norpseudoephedrine, allylsilane 3 , and catalytic amounts of trifluoromethanesulfonic acid.