Enantioselective synthesis of both enantiomers of 3-hydroxy-4, 4-dimethyl-1-phenyl-2-pyrrolidinone

P Camps, F Pérez, N Soldevilla

Index: Camps, Pelayo; Perez, Francesc; Soldevilla, Nuria Tetrahedron Letters, 1999 , vol. 40, # 37 p. 6853 - 6856

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Citation Number: 19

Abstract

The chiral auxiliaries (R)-and (S)-3-Hydroxy-4, 4-dimethyl-1-phenyl-2-pyrrolidinone were obtained in good yield and ee by enantioselective reduction of 4, 4-dimethyl-1- phenylpyrrolidine-2, 3-dione with (−)-and (+)-B-chlorodiisopinocamphenylborane,(−)-and (+)- DIP-Chloride®, respectively. The (R)-enantiomer was also obtained by enantioselective hydrogenation of the same precursor using a complex of 1, 5-cyclooctadiene Rh (I) and ( ...