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Enantioselective Desymmetrizations of Diesters to Synthesize Fully Substituted Chiral Centers of 3,4‐Dihydrocoumarins and Related Compounds
Author(s) -
Kelley Amber M.,
Haywood Rhashanda D.,
White Jonathan C.,
Petersen Kimberly S.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202000312
Subject(s) - desymmetrization , enantioselective synthesis , yield (engineering) , phosphoric acid , chemistry , intramolecular force , chiral auxiliary , catalysis , organic chemistry , combinatorial chemistry , stereochemistry , materials science , metallurgy
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).