期刊
TETRAHEDRON LETTERS
卷 43, 期 5, 页码 829-832出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(01)02247-X
关键词
nitrones; aldoximes; conjugate additions; Lewis acid catalysts; R,R-DBFOX Ph ligand; zinc(II) perchlorate; aqua complex; enantioselective reactions
Conjugate addition reactions of aldoximes to 3-crotonoyl-2-oxazolidinone and to 1-crotonoyl-3-phenyl-2-imidazolidinone are accelerated in the presence of a catalytic amount of Lewis acids. Among the chiral metal complexes with DBFOX: Ph, BOX/Bu-t, BOX/Ph, BOX/o-OHBn, Pybox, or TADDOL ligands, the most effective thus far is the aqua complex derived from R,R-DBFOX/Ph end Zinc(II) perchlorate. The reaction of 2-furancarbaldehyde oxime in dichloromethane in the presence of the R,R-DBFOX/Ph aqua complex derived from zinc(II) perchlorate hexahydrate (10 mol%) gave a moderate enantioselectivity of 64% ee at 0degreesC. Reactions using other metal complexes are also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
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