INDUSTRIAL ASYMMETRIC-SYNTHESIS BY USE OF METAL-BINAP CATALYSTS

This article covers the history and present progress of the industrial asymmetric synthesis by use of BINAP (2,2'-bis (diphenylphosphino)-1, 1'-binaphthyl)-metal catalysts. Especially, the historic discovery of the BINAP-rhodium(I)-catalyzed 1,3-hydrogen migration of N,N-diethylge ranylamine (GDEA) and the achievement of practical preparation of opti cally active BINAP, led to the establishment of the fuse industrial pr ocess for efficient production of l-menthol employing asymmetric catal ysts. Continuing efforts have been devoted to the exploration of new c atalytic reactions using new BINAP-metal complexes and their applicati ons to industrial asymmetric synthesis. Among them, asymmetric hydroge nation of functionalyzed olefins and ketones by use of BINAP-ruthenium (II) complexes provides fruitful results. Today, a wide range of chir al compounds including the pharmaceutical intermediates 4-acetoxy-2-az etidinone (4-AA) and 1,2-propanediol (2-PPD) are produced in industria l scale in Takasago.