Journal
ACS CATALYSIS
Volume 7, Issue 2, Pages 1053-1056Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03248
Keywords
pyrroloindolines; palladium catalysis; dearomatization; indoles; [3+2] cycloaddition; vinylaziridines
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Funding
- CSIRO
- University of Wollongong
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An 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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