Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 23, Pages 16815-16823Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02037
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Funding
- National Natural Science Foundation of China [21202059]
- Jilin Province Science & Technology Sustentation Program [20200404104Y]
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An efficacious method utilizing BINOL-type chiral imidodiphosphoric acid as catalyst was developed for the asymmetric [5 + 1] annulation reaction between 2-pyrrolylphenol and 1-methylindoline-2,3-dione, leading to a range of enantioenriched spiro[3,2'-morpholine-oxindole] derivatives incorporating a tertiary stereocenter with moderate to excellent yields and enantioselectivities under mild conditions.
An efficacious method in which BINOL-type chiral imidodiphosphoric acid catalyzed the asymmetric [5 + 1] annulation reaction of 2-pyrrolylphenol with 1-methylindoline-2,3-dione was established. The strategy tolerated a broad substrate scope, and 30 examples were obtained. A range of enantioenriched spiro[3,2'-morpholine-oxindole] derivatives which incorporate a tertiary stereocenter, with moderate to excellent yields (up to 96%) and enantioselectivities (up to 99%) under mild conditions, was delivered.
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