Organocatalytic Asymmetric Hetero-Diels–Alder Reaction of in Situ Generated Dienes: Access to α,β-Unsaturated δ‑Lactones Featuring CF3‑Substituted Quaternary Stereocenter

Chiral bifunctional urea-catalyzed asymmetric direct hetero-Diels–Alder reaction between alkylidene azlactone-derived dienes and trifluoromethyl aryl ketones is reported for the first time. The direct hetero-Diels–Alder reaction followed by ring opening results in densely functionalized α,β-unsatura...

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Published inJournal of organic chemistry Vol. 85; no. 5; pp. 3202 - 3212
Main Authors Joshi, Harshit, Yadav, Ankit, Das, Arko, Singh, Vinod K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.03.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETONE
FLUORINE
EQUILIBRIUM ACIDITIES
ALDEHYDES
DERIVATIVES
OLEFINIC AZLACTONES
UREA
CONJUGATE ADDITION
MICHAEL ADDITION
ENALS
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Summary:Chiral bifunctional urea-catalyzed asymmetric direct hetero-Diels–Alder reaction between alkylidene azlactone-derived dienes and trifluoromethyl aryl ketones is reported for the first time. The direct hetero-Diels–Alder reaction followed by ring opening results in densely functionalized α,β-unsaturated δ-lactones featuring a CF3-substituted quaternary stereocenter in high yields with excellent enantioselectivities. The method is compatible over a range of substrates. Moreover, the reaction is scaled up and the α,β-unsaturated δ-lactones were converted to amino acid derivatives decorated with trifluoromethylated carbinol functionality.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03076