Premium
Planar chiral ferrocenes as ligands in the vanadium‐catalyzed asymmetric epoxidation of allylic alcohols
Author(s) -
Bolm Carsten,
Kühn Toralf
Publication year - 2002
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1560/ymyd-ff4y-mb9c-efte
Subject(s) - chemistry , allylic rearrangement , vanadium , ferrocene , oxazoline , sulfoxide , catalysis , enantioselective synthesis , metalation , medicinal chemistry , epoxide , hydroxamic acid , combinatorial chemistry , stereochemistry , organic chemistry , electrochemistry , electrode
Starting from either ( S )‐4‐ tert ‐butyl‐2‐ferrocenyl‐2‐oxazoline or ( S )‐ S ‐ferrocenyl‐ S ‐4‐tolyl sulfoxide, new planar chiral hydroxamic acids have been synthesized employing the directed ortho ‐metalation strategy. The ferrocene‐derived hydroxamic acids are capable of serving as ligands in the vanadium‐catalyzed asymmetric epoxidation of allylic alcohols, furnishing the epoxide of 2‐methyl‐3‐phenylprop‐2‐en‐1‐ol with up to 34% ee.