The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3‑Nitroindoles
journal contribution
posted on 2016-12-27, 00:00 authored by Daniel
J. Rivinoja, Yi Sing Gee, Michael G. Gardiner, John H. Ryan, Christopher J. T. HylandAn
efficient, diastereoselective synthesis of densely functionalized
pyrroloindolines is reported. The reaction proceeds via cycloaddition
of a vinylaziridine-derived Pd-stabilized 1,3-dipole to electron-deficient
3-nitroindoles. The reactions give the trans diastereoisomer
with high selectivity; however, when a 4-substituent is present on
the indole ring, a reversal of diastereoselectivity is observed.
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Keywords
4- substituentselectivityvinylaziridine-derivedtrans diastereoisomerDiastereoselective Synthesiscycloadditionindole ringPd-Catalyzed Dearomative Cycloadditiondiastereoselectivityfunctionalized pyrroloindolinesPd-stabilizedelectron-deficient 3- nitroindolesreaction proceedsPyrroloindolineNitroindole1- Tosyl -2-vinylaziridinereversaldiastereoselective synthesis
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