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Abstract:
We report a general approach to highly functionalized (Z)-allylic amines by decarboxylative allylation of vinyloxazolidin-2-ones. This process engages sodium sulfinates as nucleophiles to form a new carbon-sulfur bond, utilizing a palladium catalyst generated from Pd(OAc)(2) and diphosphine ligand dpppe. The scope of the protocol is illustrated by the synthesis of 30 representative allylic amines with high regio- and stereoselectivity. Mechanistic studies show that the Z-selectivity of the reaction stems from the formation of a palladacycle intermediate through Pd-N chelation. The synthetic utility of this method was further exemplified by the gram-scale synthesis and subsequent transformations to various compounds.
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CHEMICAL COMMUNICATIONS
ISSN: 1359-7345
Year: 2023
Issue: 65
Volume: 59
Page: 9892-9895
4 . 3
JCR@2023
4 . 3 0 0
JCR@2023
ESI Discipline: CHEMISTRY;
ESI HC Threshold:39
JCR Journal Grade:2
CAS Journal Grade:3
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ESI Highly Cited Papers on the List: 0 Unfold All
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30 Days PV: 0
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