3‐Arylsulfonyloxazolidines as Chiral Templates; Asymmetric Synthesis of 2‐Substituted 2‐Hydroxycyclohexanecarbaldehydes from 2‐Hydroxymethylenecyclohexanone

Abstract

Two new stereogenic centers are formed upon condensation of the sulfamide 1 with the enol 2 to give the oxazolidine 3, which, in turn, adds carbanion derivatives MNu with high diastereofacial selectivity to give 4. Cleavage of the chiral auxiliary with 1,3-propanedithiol leads to diastereo- and enantiomerically pure aldehyde derivatives 5. All steps proceed practically stereo specifically.