Tetrahedron Letters p. 6703 - 6706 (1990)
Update date:2022-08-11
Topics:
Leonard
Hewitt
Ouali
Simpson
Newton
The monoketal derived from cis-bicyclo[3.3.0]octane-3,7-dione was converted to epoxides 3. Meso exo epoxide was cleaved via enantioselective deprotonaiton using chiral lithium amide bases to provide the synthetically useful alcohol 7 with up to 76%ee. The enantiomeric excess of the alcohol was determined by 1H NMR chiral shift techniques.
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