Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 18, Pages 8638-8644Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5013724
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Funding
- Spanish DGICYT [CTQ 2011-28487]
- JC y L [VA064U13]
- University of Valladolid
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Enantioenriched trisubstituted lactones were obtained in good yields and moderate to very good enantioselectivities in one-pot process, which implies a sequential organocatalyzed Michael addition of ketones to enals, followed by catalytic intramolecular diastereoselective Tishchenko reaction and lactonization. The final lactones were obtained as single diastereoisomers, demonstrating that the mixture of the anti and syn diastereomers epimerized to the syn hydroxy ester during the oxido-reduction step.
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