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Asymmetric Synthesis of Allylamines by Regio- and Diastereo- Selective 1,2-Addition of Organolithium Reagents to Conjugated Sulfinimines

par Loison, Anaïs ;Rossi, Nicolò ;Evano, Gwilherm
Référence Journal of organic chemistry, 91
Publication A Paraître, 2026-06-05

Article révisé par les pairs

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Résumé :

practical, robust and straightforward access to optically enriched allylamines by a regio- and diastereo- selective 1,2-addition of organolithium reagents to Davis-Ellman-type chiral conjugated sulfinimines is reported. The procedure is operationally simple, proceeds under mild conditions, requires readily available starting materials and consistently delivers complete regiocontrol in favor of 1,2-addition. Synthetically useful levels of diastereoselectivity can be obtained in all cases and the reaction tolerates a broad range of organolithium reagents and substitution patterns on the sulfinimine. The method further enables a one-pot 1,2-addition/N-functionalization sequence through in situ trapping of the transient lithiated sulfinamide, constituting a formal 1,2-difunctionalization of the C=N bond and expanding the structural diversity accessible in a single operation.