Enantioselective Synthesis of 5‑Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis

The first enantioselective formal [3 + 2] cycloaddition between α-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is...

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Published inJournal of organic chemistry Vol. 84; no. 1; pp. 314 - 325
Main Authors Martínez-Pardo, Pablo, Blay, Gonzalo, Vila, Carlos, Sanz-Marco, Amparo, Muñoz, M. Carmen, Pedro, José R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.01.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
UPDATE 1
ASYMMETRIC ALDOL REACTION
METHYL ISOCYANOACETATE
PLATINUM(II) COMPLEXES
SELF-DISPROPORTIONATION
CHIRAL BIS(OXAZOLINE) LIGANDS
AMINO-ACIDS
PROCHIRAL KETONES
CYCLIC-PEPTIDES
OXAZOLINES
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Summary:The first enantioselective formal [3 + 2] cycloaddition between α-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo- and enantioselectivity.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02808