Ligand Control of Diastereodivergency in Asymmetric Inverse Electron Demand Diels–Alder Reaction

A diastereodivergent direct catalytic asymmetric inverse electron demand Diels–Alder reaction between ketenes and 3-alkylenyloxindoles was accomplished by using chiral N,N′-dioxide/gadolinium complexes. By adjusting only the substituents of the ligand and retaining other catalysis conditions, both s...

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Bibliographic Details
Published inACS catalysis Vol. 5; no. 10; pp. 6052 - 6056
Main Authors Hao, Xiaoyu, Lin, Lili, Tan, Fei, Yin, Chengkai, Liu, Xiaohua, Feng, Xiaoming
Format Journal Article
LanguageEnglish
Published American Chemical Society 02.10.2015
Subjects
indole-fused dihydropyranones
asymmetric catalysis
diastereodivergent
N,N′-dioxide/gadolinium complexes
inverse electron demand Diels−Alder reaction
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Summary:A diastereodivergent direct catalytic asymmetric inverse electron demand Diels–Alder reaction between ketenes and 3-alkylenyloxindoles was accomplished by using chiral N,N′-dioxide/gadolinium complexes. By adjusting only the substituents of the ligand and retaining other catalysis conditions, both syn- and anti-indole-fused dihydropyranones bearing two vicinal stereogenic centers were obtained in high yields with excellent ee values. Thus, by changing the configuration of the chiral ligands, all stereoisomers could be obtained from the same set of starting materials.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.5b01719