Construction of Acyclic Quaternary Stereocenters via Mannich-Type Addition of α,α-Disubstituted N-tert-Butanesulfinyl Ketimines to Isatin-Derived Ketimines.
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DOI: 10.1021/acs.orglett.2c00888
Abstract: A Mannich reaction of deprotonated, highly enantioenriched α,α-disubstituted N-tert-butanesulfinyl ketimines with isatin-derived ketimines was developed to prepare 3-amino-3-substituted oxindoles bearing an acyclic quaternary stereogenic carbon substituted with two sterically similar groups. The excellent stereocontrol of… read more here.
Keywords: butanesulfinyl ketimines; ketimines isatin; disubstituted tert; tert butanesulfinyl ... See more keywords
Stereoselective Electrophilic α-Alkynylation of α,α-Disubstituted N-tert-Butanesulfinyl Ketimines for Construction of Less Accessible Acyclic Quaternary Stereocenters.
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DOI: 10.1021/acs.orglett.2c03865
Abstract: In order to construct less accessible acyclic quaternary stereocenters, a protocol was developed to α-alkynylate α,α-disubstituted N-tert-butanesulfinyl ketimines stereoselectively using 1-(2-trimethylsilylethynyl)-1,2-benziodoxol-3(1H)-one in the presence of fluoride. Despite the steric and electrical similarity between the two… read more here.
Keywords: quaternary stereocenters; disubstituted tert; alkynylation; less accessible ... See more keywords