Efficient Procedures for the Large‐Scale Preparation of (1S,2S)‐trans‐ 2‐Methoxycyclohexanol, a Key Chiral Intermediate in the Synthesis of Tricyclic β‐Lactam Antibiotics.

Abstract Enzymatic and chemical resolution methods suitable for preparation of multi-kg quantities of (+)-(1S,2S)-2-methoxycyclohexanol from (+/−) trans-2-methoxycyclohexanol have been developed. The enzymatic resolution was found to offer a particularly simple process affording the resolved product in good yield and excellent enantiomeric excess and has now been operated consistently on a manufacturing scale.