A Convenient Practical Method for the Preparation of (-)-(1 S, 2 S)-5-Norbornene-2-carboxylic Acid, Incorporating Efficient Recovery of the Chiral Auxiliary d- …

…, L Zhou, RD McCargar, T Mahmud, I Hirst

Index: Chang, HeXi; Zhou, Li; McCargar, Robert D.; Mahmud, Tanvir; Hirst, Ian Organic Process Research and Development, 1999 , vol. 3, # 4 p. 289 - 291

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Citation Number: 12

Abstract

Enantiomerically pure (−)-(1S,2S)-5-norbornene-2-carboxylic acid (3), a key intermediate in the synthesis of some adenosine receptor antagonists, 1 has generally been prepared by Diels−Alder reaction of cyclopentadiene with a chiral auxiliary functionalized acrylate (1), followed by saponification (see Scheme 1). Choosing a suitable chiral auxiliary has been the focus of many researchers. Even though dihydroxylated dispiroketal, 2 cis-1-arylsulfonamido-2- ...