Chiral Lewis Acid-Catalyzed Asymmetric Multicomponent Michael Reaction through [1,2]-Phospha-Brook Rearrangement

The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and 4-oxobutenoates was realized. A series of oxindole derivatives containing two contiguous stereocenters was obtained in high yields and excellent stereosele...

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Published inOrganic letters Vol. 25; no. 34; pp. 6262 - 6266
Main Authors Lin, Qianchi, Wang, Siyuan, Weng, Rui, Cao, Weidi, Feng, Xiaoming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.09.2023
Amer Chemical Soc
Subjects
catalysts
chemical reactions
Chemistry
Chemistry, Organic
Lewis acids
Physical Sciences
Science & Technology
CHEMISTRY
CYCLOADDITION
ALPHA-KETOESTERS
LIGANDS
ISATINS
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Summary:The multicomponent catalytic asymmetric Pudovik addition/[1,2]-phospha-Brook rearrangement/Michael reaction sequence of isatins, phosphites, and 4-oxobutenoates was realized. A series of oxindole derivatives containing two contiguous stereocenters was obtained in high yields and excellent stereoselectivities (up to >99% yield, >95:5 dr, >99% ee) using a chiral Lewis acid catalyst. A possible catalytic model is presented to illustrate the stereocontrol.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.3c02042