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Enantioselective Synthesis of Chiral Homoallyl Alcohols and Homoallylamines by Nucleophilic Addition of an Allylboron Reagent Modified by a Polymer‐Supported Chiral Ligand
Author(s) -
Itsuno Shinichi,
Watanabe Katsuhiro,
ElShehawy Ashraf A.
Publication year - 2001
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(20010129)343:1<89::aid-adsc89>3.0.co;2-6
Subject(s) - chemistry , enantioselective synthesis , enantiopure drug , divinylbenzene , chiral ligand , reagent , chiral derivatizing agent , organic chemistry , polymer , nucleophile , monomer , combinatorial chemistry , styrene , copolymer , polymer chemistry , enantiomer , chiral column chromatography , catalysis
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.