Development of Chiral, Bifunctional Thiosquaramides: Enantioselective Michael Additions of Barbituric Acids to Nitroalkenes

We report a general method for the synthesis of chiral thiosquaramides, a class of bifunctional catalysts not previously described in the literature. Thiosquaramides are found to be more acidic and significantly more soluble in nonpolar solvents than their oxosquaramide counterparts, and they are ex...

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Published inJournal of the American Chemical Society Vol. 139; no. 15; pp. 5297 - 5300
Main Authors Rombola, Michael, Sumaria, Chintan S., Montgomery, Thomas D., Rawal, Viresh H.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 19.04.2017
Subjects
Alkenes - chemistry
Barbiturates - chemistry
Chemistry
Chemistry, Multidisciplinary
Molecular Structure
Nitro Compounds - chemistry
Physical Sciences
Quinine - analogs & derivatives
Quinine - chemical synthesis
Quinine - chemistry
Science & Technology
Stereoisomerism
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
HYDROGEN
BOND DONORS
DESIGN
ORGANOCATALYSTS
EQUILIBRIUM ACIDITIES
CARBOXAMIDES
PROTON
DERIVATIVES
UREA
CATALYST ACIDITY
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Summary:We report a general method for the synthesis of chiral thiosquaramides, a class of bifunctional catalysts not previously described in the literature. Thiosquaramides are found to be more acidic and significantly more soluble in nonpolar solvents than their oxosquaramide counterparts, and they are excellent catalysts for the unreported, enantioselective conjugate addition reaction of the barbituric acid pharmacaphore to nitroalkenes, delivering the chiral barbiturate derivatives in high yields and high enantioselectivities, even with catalyst loadings as low as 0.05 mol%.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b01115