5870-87-1Relevant articles and documents
Enantioselective Saponification of Diacetates of 2-Nitro-1,3-propanediols by Pig-Liver Esterase and Preparation of Enantiomerically Pure Derivatives of 2-Nitro-allylic Alcohols (Chiral Multiple-Coupling Reagents)
Eberle, Martin,Egli, Martin,Seebach, Dieter
, p. 1 - 23 (2007/10/02)
The reproducible enantioselective saponification of open-chain and cyclic diacetates of meso-2-nitro-1,3-propanediols (see 4b-13b) with pig-liver esterase (PLE) gives monoacetates (see 4c-13c) of >95percent enantiomeric excess.The Re enantiotopic acetate group appears to be saponified preferentially, as proved by the X-ray crystal structure analysis of three camphanoates 4d, 6d, and 7d.Elimination of H2O or AcOH from the hydroxy acetates thus available gives derivatives of nitro-allylic alcohols (see 20-24, 27, and 29) which are subjected to diastereoselective Michael additions or SN2' substitutions.
