Journal of Organic Chemistry p. 3018 - 3027 (1987)
Update date:2022-08-04
Topics: Asymmetric synthesis Tartaric acid Chiral Auxiliary 2-Alkyl-2-arylacetic Acids
Castaldi, Graziano
Cavicchioli, Silvia
Giordano, Claudio
Uggeri, Fulvio
A highly enantioselective synthesis of 2-alkyl-2-arylacetic acids, an important class of antiinflammatory agents, based on a new diastereoselective α-bromination of homochiral acetals 1 and on the stereospecific silver-promoted rearrangement of the corresponding homochiral α-bromo acetals 2 and 3, is reported.The new methodology represents a meaningful example of the use of tartaric acid as efficient and economic chiral auxiliary.The asymmetric bromination of 1 is of general character and occurs with very high diastereoselectivity, even at room temperature; a mechanism for the new reaction is proposed.The overall process has been successfully applied to the preparation of enantiomerically pure 2-alkyl-2-arylacetic acids, among them (2S)-(+)-2-(6-methoxy-2-naphthyl)propanoic acid (Naproxen)
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Doi:10.1021/jm00386a010
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(1996)Doi:10.1007/BF01148635
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(1963)Doi:10.1055/s-2008-1067152
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