Studies on the Terpenoids and Related Alicyclic Compounds. Part XLI. Stereoselective Synthesis of Both Half Segments for (-)-Sarcophytonin A and (-)-Sarcophytoxide.
“…This finding considerably widens the synthetic scope of the tandem conjugate addition−trapping of electrophile. Among the many possible reactions of these silyl enol ethers, we have performed the reactions to form the following interesting enantiomerically enriched synthons (Scheme ). − It should be pointed out, that these transformations could not be accomplished directly from the zinc enolate. 2 …”
[formula: see text] The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCI and NEt3. These enantiomerically enriched silyl enol ethers were submitted to four synthetic transformations to show their synthetic utility. The zinc enolates obtained from acyclic enones were found to be configurationally stable, as shown by the stereochemistry of the silyl enol ethers.
“…This finding considerably widens the synthetic scope of the tandem conjugate addition−trapping of electrophile. Among the many possible reactions of these silyl enol ethers, we have performed the reactions to form the following interesting enantiomerically enriched synthons (Scheme ). − It should be pointed out, that these transformations could not be accomplished directly from the zinc enolate. 2 …”
[formula: see text] The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCI and NEt3. These enantiomerically enriched silyl enol ethers were submitted to four synthetic transformations to show their synthetic utility. The zinc enolates obtained from acyclic enones were found to be configurationally stable, as shown by the stereochemistry of the silyl enol ethers.
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