Helvetica Chimica Acta p. 1 - 23 (1988)
Update date:2022-07-31
Topics:
Eberle, Martin
Egli, Martin
Seebach, Dieter
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.
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