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C2-Symmetric 4,4′,5,5′-Tetrahydrobi(oxazoles) and 4,4′,5,5′-Tetrahydro-2,2′-methylenebis[oxazoles] as Chiral Ligands for Enantioselective Catalysis Preliminary Communication

✍ Scribed by Dieter Müller; Gisela Umbricht; Beat Weber; Andreas Pfaltz

Book ID
102859314
Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
517 KB
Volume
74
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The synthesis of a series of enantiomerically pure, C~2~‐symmetric 4,4′,5,5′‐tetrahydro‐2,2′‐methylenebis[oxazoles] and 4,4′,5,5′‐tetrahydro‐2,2′‐bi(oxazoles) is reported. Copper complexes with anionic tetrahydromethylenebis[oxazole] ligands are efficient catalysts for the enantioselective cyclopropane formation from olefins and diazo compounds (up to 96% ee in the reaction of styrene with menthyl diazoacetate). Tetrahydrobi(oxazole)iridium(I) complexes were found to catalyze transfer hydrogenations of aryl alkyl ketones with i‐PrOH (up to 91% ee). Tetrahydrobi(oxazole)palladium complexes can be used as enantioselective catalysts for allylic nucleophilic substitution (up to 77% ee in the reaction of PhCHCHCH(OAc)Ph with NaHC(COOMe)~2~).

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