New Efficient Route to the Synthesis of Enantiopure (+) and (‐) Bicyclo[2.2.1]heptan‐syn‐2,7‐diol Using Lipase‐Catalyzed Transesterifications.

Abstract

Bridged compounds Q 0060New Efficient Route to the Synthesis of Enantiopure (+) and (-) Bicyclo[2.2.1]heptan-syn-2,7-diol Using Lipase-Catalyzed Transesterifications. -Starting from the racemic bicyclo[2.2.1]hept-5-en-2-ol (I), an alternative and efficient route to title compounds (+)-(VI), useful as potential chiral auxiliary for asymmetric syntheses, is reported. The overall enantiomeric excess is described with up to 99%. (-)-(VI) is obtained after hydrolysis of (III) following the same sequence with similar yields. -(MARTINS, J. E. D.; DE OLIVEIRA, L. F.; COSTA*, V. E. U.; Synth. Commun. 36 (2006) 22-24, 3419-3424; Inst. Quim., Univ. Fed. Rio Grande do Sul,