(Z,1S,10aR)-(−)-Menthyl 1-hydroxy-1,2,3,5,6,7,10,10a-octahydropyrrolo[1,2-a]azocine-10a-carboxylate

Abstract

The structure determination confirms the stereochemistry of the title compound, C21H35NO3, obtained as an intermediate in the enantioselective synthesis of deoxynojirimicine analogs. The system contains a pyrrolo[1,2-a]azocine backbone, which was synthesized by a domino process involving a [2,3]-sigmatropic rearrangement. The incorporation of a chiral auxiliary (−)-menthyl, whose stereocentres are not involved during the synthesis, enables the assignation of absolute configuration. The crystal structure features O—H...O hydrogen bonds involving the hydroxy groups as donors and the carbonyl groups as acceptors, which link the molecules into chains running along [010].