506441-57-2Relevant articles and documents
Asymmetric synthesis of half-cage alcohol compounds
Alifantes, Joao,Nichele, Aline G.,Costa, Valentim E.U.
, p. 2019 - 2024 (2007/10/03)
To obtain enantiopure pentacyclic chlorinated and dechlorinated alcohols, we evaluated various synthetic routes. Enantiopure acetate (-)-5 (ee >95%) was obtained from an enantioselective inversion of a stereogenic center of the pentacyclic acetate (+)-4 in an acidic medium. Conversely, enantiopure alcohols (+)-11 and (+)-15 were obtained by the kinetic resolution of alcohol (±)-11 by transesterification using lipase from Candida rugosa. It was verified that the lipase recognized alcohol (±)-11, producing the alcohol (+)-11 (ee >98%) and acetate (-)-13 (ee >99%) with a high degree of enantioselectivity (E >100) and a conversion of 50% after only 1 h.