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Enantioselective conjugate additions of aldoximes to 3-crotonoyl-2-oxazolidinone and 1-crotonoyl-3-phenyl-2-imidazolidinone catalyzed by the aqua complex between R,R-DBFOX/Ph and zinc(II) perchlorate

✍ Scribed by Kimitaka Nakama; Sumito Seki; Shuji Kanemasa

Book ID
104232288
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
232 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 and 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 0Β°C. Reactions using other metal complexes are also discussed.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Enantioselective Co
ChemInform Abstract: Enantioselective Conjugate Additions of Aldoximes to 3-Crotonoyl-2-oxazolidinone and 1-Crotonoyl-3-phenyl-2-imidazolidinone Catalyzed by the Aqua Complex Between R,R-DBFOX/Ph and Zinc(II) Perchlorate.
✍ Kimitaka Nakama; Sumito Seki; Shuji Kanemasa πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 32 KB

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