Journal
CHEMISTRYSELECT
Volume 5, Issue 10, Pages 3018-3022Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202000312
Keywords
Chiral Phosphoric Acid; Desymmetrization; 3,4-Dihydrocoumarin; 1,4-Dioxanone; 1,4-Morpholinone
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Funding
- National Institutes of Health [GM116041]
- National Center for Complementary and Integrative Health of the National Institutes of Health [5T32 AT008938]
- National Institutes of Health (University of North Carolina at Greensboro)
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In this communication, a preparation of novel enantioenriched 1,4-dioxanones, 1,4-morpholinones and 3,4-dihydrocoumarins is described. The outlined procedure utilizes a desymmetrization strategy of prochiral diesters whereby a chiral phosphoric acid catalyzes an intramolecular lactonization to yield enantioenriched fully substituted chiral centers. This desymmetrization strategy yielded various lactones with excellent to moderate enantioselectivity and yields (12 examples up to 99% ee and 96% yield).
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