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DOI: 10.1055/a-2223-3803
Stereoselective Construction of Vicinal Quaternary Stereocenters via the 1,6-Conjugate Addition of β,β-Disubstituted N-Sulfinyl Metalloenamines to Isatin-Derived para-Quinone Methides
This work was supported by the National Natural Science Foundation of China (22361049 and 22161048) and the ‘Double Thousand Plan’ of Jiangxi Province (JXSQ2023102241).
Abstract
A 1,6-conjugate addition reaction of β,β-disubstituted N-tert-butanesulfinyl metalloenamines, generated via stereospecific α-deprotonation of enantioenriched α,α-disubstituted ketimines or deprotonation of the NH in geometry-defined enesulfinamides, with isatin-derived para-quinone methides is developed to build vicinal quaternary stereocenters with high stereocontrol. The resulting 3,3-disubstituted oxindoles contain a less-accessible acyclic quaternary stereogenic carbon substituted with two sterically and electronically similar groups at the α-position of the imino group. This protocol constitutes a rare example of the stereoselective construction of vicinal quaternary stereocenters via the conjugate addition of acyclic enolates/aza-enolates bearing two similar β-substituents.
Key words
N-sulfinyl metalloenamines - conjugate addition - deprotonation - quaternary stereocenter - stereoselectivitySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2223-3803.
- Supporting Information
Publikationsverlauf
Eingereicht: 13. November 2023
Angenommen nach Revision: 06. Dezember 2023
Accepted Manuscript online:
06. Dezember 2023
Artikel online veröffentlicht:
16. Januar 2024
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