The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles

Daniel J. Rivinoja; Yi Sing Gee; Michael G. Gardiner; John H. Ryan; Christopher J.T. Hyland

doi:10.1021/acscatal.6b03248

The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles

Daniel J. Rivinoja, Yi Sing Gee, Michael G. Gardiner, John H. Ryan, Christopher J.T. Hyland

Research output: Contribution to journal › Article › Research › peer-review

98 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1053-1056
Number of pages	4
Journal	ACS Catalysis
Volume	7
Issue number	2
DOIs	https://doi.org/10.1021/acscatal.6b03248
Publication status	Published - 3 Feb 2017
Externally published	Yes

Keywords

dearomatization
indoles
palladium catalysis
pyrroloindolines
vinylaziridines
[3 + 2] cycloaddition

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10.1021/acscatal.6b03248

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title = "The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles",

abstract = "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.",

keywords = "dearomatization, indoles, palladium catalysis, pyrroloindolines, vinylaziridines, [3 + 2] cycloaddition",

author = "Rivinoja, {Daniel J.} and Gee, {Yi Sing} and Gardiner, {Michael G.} and Ryan, {John H.} and Hyland, {Christopher J.T.}",

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doi = "10.1021/acscatal.6b03248",

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T1 - The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles

AU - Rivinoja, Daniel J.

AU - Gee, Yi Sing

AU - Gardiner, Michael G.

AU - Ryan, John H.

AU - Hyland, Christopher J.T.

PY - 2017/2/3

Y1 - 2017/2/3

N2 - 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.

AB - 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.

KW - dearomatization

KW - indoles

KW - palladium catalysis

KW - pyrroloindolines

KW - vinylaziridines

KW - [3 + 2] cycloaddition

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DO - 10.1021/acscatal.6b03248

M3 - Article

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SN - 2155-5435

VL - 7

SP - 1053

EP - 1056

JO - ACS Catalysis

JF - ACS Catalysis

IS - 2

ER -

The Diastereoselective Synthesis of Pyrroloindolines by Pd-Catalyzed Dearomative Cycloaddition of 1-Tosyl-2-vinylaziridine to 3-Nitroindoles

Abstract

Keywords

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