Efficient resolution of some monoprotected derivatives of Corey lactone
Racemic monoprotected at primary hydroxy group Corey lactones were resolved using (1S,2R,5R)-6,6-dimethyl-4-oxo-3-oxabicyclo-[3.1.0]hexan-2-ol as a chiral auxiliary reagent of hemiacylal chemotype.
Loza, Vladimir V.,Vostrikov, Nikolay S.,Miftakhov, Mansur S.
experimental part
p. 125 - 126
(2012/09/05)
Ozonolysis of (1R,cis)-4,7,7-trimethyl-3-oxabicyclo[4.1.0]hept-4-en-2-one
The structure of peroxides forming in ozonolysis of enololactone and their further transformations are determined by the structure of the initial substrate and by effect of solvent used for ozonolysis.
A preparation of trans- and cis-caronaldehyde derivatives is described by employing iodolactonization reaction as a key step.Investigation is also carried out to establish an asymmetric synthesis by employing the same methodology which allows diastereoselective formation of optically active intermediates in both enantiomeric forms from a single precursor though the degree of asymmetric induction is found to be less satisfactory.