Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.
نویسندگان
چکیده
COP-Cl catalyzes the rearrangement of (E)-allylic trichloroacetimidates to provide transposed allylic trichloroacetamides of high enantiopurity, a transformation that underlies the first truly practical method for transforming prochiral allylic alcohols to enantioenriched allylic amines and congeners. The high functional group compatibility of this asymmetric rearrangement and the demonstrated broad utility in synthesis of the allylic trichloroacetimidate to allylic trichloroacetamide conversion are singular features of this new catalytic asymmetric reaction.
منابع مشابه
Catalytic asymmetric rearrangement of allylic N-aryl trifluoroacetimidates. A useful method for transforming prochiral allylic alcohols to chiral allylic amines.
[reaction: see text] A useful method for the conversion of prochiral allylic alcohols to chiral allylic amines of high enantiopurity is reported. N-(4-Methoxyphenyl)trifluoroacetimidates are excellent substrates for the palladium(II)-catalyzed allylic imidate rearrangement as the allylic trifluoroacetamide products can be deprotected in two steps to provide chiral nonracemic allylic amines. Di-...
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Benzotetramisole promotes the catalytic asymmetric [2,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-α-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).
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ورودعنوان ژورنال:
- Journal of the American Chemical Society
دوره 125 41 شماره
صفحات -
تاریخ انتشار 2003