Stereoselective Construction of Less-Accessible Acyclic Quaternary Carbon Stereocenters via Rhodium-Catalyzed Allylic Alkylation of β,β-Disubstituted Enesulfinamides
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引用次数: 0
Abstract
In the presence of Wilkinson’s catalyst, the N-sulfinyl metalloenamines derived from NH-deprotonation of β,β-disubstituted enesulfinamides undergo nucleophilic allylic substitution with allyl carbonate, affording α-allylated ketimines with high stereoselectivity. These allylation products possess challenging acyclic quaternary stereocenters containing one allyl group and two alkyl groups that are both sterically and electronically similar (e.g., Me and Et). By utilizing appropriate stereoisomers of enesulfinamides, it becomes feasible to selectively access each of the four potential stereoisomers of the allylation products, thereby facilitating the selective synthesis of stereoisomers of α-tertiary chiral amines featuring a β-quaternary stereocenter through imino nucleophilic addition.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.