Stereocontrolled α-Allylation of α-Branched N-tert-Butanesulfinyl Ketimines via a Michael-Wittig Cascade for the Construction of Acyclic Quaternary Stereocenters.
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DOI: 10.1021/acs.orglett.2c03801
Abstract: A single-flask cascade of Michael addition and Wittig olefination was developed to allow the stereoselective α-allylic alkylation of α-branched N-tert-butanesulfinyl ketimines for the construction of acyclic quaternary stereocenters bearing two sterically and electronically similar substituents.… read more here.
Keywords: tert butanesulfinyl; construction acyclic; butanesulfinyl ketimines; acyclic quaternary ... 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
Tuning the Reactivity of Ketones through Unsaturation: Construction of Cyclic and Acyclic Quaternary Stereocenters via Zn-ProPhenol Catalyzed Mannich Reactions
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DOI: 10.1021/acscatal.8b04685
Abstract: Introduction of unsaturation adjacent to the carbonyl drastically improves the reactivity of the Zn-ProPhenol catalyzed Mannich reactions between N-carbamoyl imines and a-branched ketones. Despite only a small change in the substrate acidity, the bimetallic catalyst… read more here.
Keywords: cyclic acyclic; acyclic quaternary; catalyzed mannich; quaternary stereocenters ... See more keywords