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Title Synthesis of Two Chiral Biarylbisoxazoline Ligands and Their Application in Asymmetric Allylic Oxidation of Cyclohexene
Type Presentation
Keywords C2-symmetric, chiral bisoxazoline, bitolyl bisoxazoline, allylic oxidation,copper (I) hexaflurophosphate
Abstract C2-symmetric chiral bisoxazoline ligands have emerged as an efficient class of ligands in an increasing number of asymmetric transformations. [1,2]. Here in two chiral (S,S,S)-2,2′-bitolyl bisoxazoline and (S,R,S)-2,2′-bitolyl bisoxazoline ligands were synthesised in high yield and enantiomeric excess using inexpensive and available starting material 3-methyl benzoic acid. Chiral (S,S,S)-2,2′-bitolyl bisoxazoline ligand along with copper (I) hexaflurophosphate as counter ion was used as a catalyst in asymmetric allylic oxidation of cyclohexene with t-butylperbenzoate(Scheme1) [3,4]. The highest yield and optical rotation for the chiral allyl ester product was obtained in the presence of phenyhydrazine as an electron donor and molecular sieves in acetone (Scheme1) [3,4].
Researchers Davoud Asgari (Second Researcher), Parisa Eslami (Fifth Researcher), Saber Nazari (Not In First Six Researchers), Hamid Arvinnezhad (Fourth Researcher), Saadi Samadi (Third Researcher), Khosrow Jadidi (First Researcher)