The highly stereoselective conjugate addition of nitromethane to α,β-unsaturated cyclobutyl esters derived from (-)-(S)-verbenone has been executed to afford the adducts as single stereoisomers in good yields. These products furnish cyclobutyl GABA analogues and γ-lactams which, in turn, can be used as precursors of pyrrolidines. Moreover, both the enantiopure γ-nitro esters and the derived γ-amino esters are potentially useful for incorporation into γ-amino peptidomimetics. © 2002 Elsevier Science Ltd. All rights reserved.
|Publication status||Published - 5 Apr 2002|