ABSTRACT
While a great deal of emphasis has been placed upon the synthesis of rigid benzocycloalk-1 -ene derived cis-1 -amino-2-alcohols,3 practical processes remained elusive until recently.4 The chiral 1,2 dioxygen benzocycloalkanes have become available by asymmetric epoxidation of the corresponding prochiral olefins l .5 These adducts were utilized as excellent precursors for the synthesis of as-aminoalcohols 2 using appropriate selective amination processes (Scheme 2). Research in this field of unfimctionalized asymmetric epoxidation has been driven both by the recognized utility of optically active epoxides in organic synthesis6 and by widespread interest in the mechanism of oxygen atom transfer from metals to alkenes.6,7 As a result, the development of synthetic catalysts that provide practical access to such compounds has constituted a major emphasis in the field of asymmetric catalysis and recently chiral (salen)Mnbased complexes were developed as catalysts for asymmetric epoxidations of prochiral olefins.6 This chapter focuses on the development of a practical chiral (salen)Mn catalyst for asymmetric epoxidation for unfunctionalized alkenes, and a practical application of (salen)Mn-based epoxidation methodology to the synthesis of enantiopure cw-aminoindanol and its application to drug synthesis.
