Synthesis of 3‐ and 4‐Hydroxy‐2‐aminocyclohexanecarboxylic Acids by Iodocyclization

Abstract

Abstract Starting from cis ‐7‐azabicyclo[4.2.0]oct‐4‐en‐8‐one, novel routes have been developed for the synthesis of 2‐amino‐4‐hydroxycyclohexanecarboxylic acid and its 3‐hydroxy‐substituted analog via iodooxazine, iodooxazoline or iodolactone intermediates. After CAL‐B‐catalyzed enzymatic transformation of the starting β‐lactam, the iodolactone method was applied to the synthesis of 3‐hydroxy‐substituted β‐amino acid enantiomers. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)