Enamtioselective allylation of N-(trimethylsilyl)benzaldlehyde imine using polymer-supported chiral allylboron reagents
Polymer-supported chiral N-sulfonylamino alcohols 3 and 4 obtained from copolymerization of enantiomerically pure amino alcohols 1c and 2c derived from (1R)-(+)-camphor with styrene and divinylbenzene were treated with triallylborane, trimethallylborane,
Enantioselective Synthesis of Chiral Homoallyl Alcohols and Homoallylamines by Nucleophilic Addition of an Allylboron Reagent Modified by a Polymer-Supported Chiral Ligand
Crosslinked polymer-supported chiral N-sulfonylamino alcohols 5-8 have been prepared by suspension polymerization of enantiopure N-sulfonylamino alcohol monomers 1-4 with styrene and divinylbenzene. Polymer-supported chiral allylboron reagents were prepared from the polymeric chiral ligands. Enantioselective additions of the polymer-supported allylboron reagents to aldehydes and N-(trimethylsilyl)imines have been successfully carried out in the heterogeneous system. The corresponding optically active homoallyl alcohols and homoallylamines were obtained in high yields with high enantioselectivities (up to 95% ee) which are almost the same as those obtained from homogeneous analogues. The polymer-supported chiral ligands used were recovered easily and can be reused without any loss of activity.
Itsuno, Shinichi,Watanabe, Katsuhiro,El-Shehawy, Ashraf A.
p. 89 - 94
(2007/10/03)
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