Iridium-catalyzed intramolecular enantioselective c-h alkylation at the C-2 position of N-alkenylindoles

Takanori Shibata; Naoto Ryu; Hideaki Takano

doi:10.1002/adsc.201401163

Iridium-catalyzed intramolecular enantioselective c-h alkylation at the C-2 position of N-alkenylindoles

Takanori Shibata^*, Naoto Ryu, Hideaki Takano

^*Corresponding author for this work

School of Advanced Science and Engineering

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

61 Citations (Scopus)

Abstract

Intramolecular enantioselective alkylation of N-alkenylindoles proceeded via C-H bond cleavage at the C-2 position in the presence of a cationic iridium catalyst with a diphosphine ligand. Aroyl groups at the C-3 position of the indoles operated as effective directing groups, and chiral 1-substituted-2,3-dihydro-1H-pyrrolo[1,2-a]indoles were obtained in high yield with excellent ee.

Original language	English
Pages (from-to)	1131-1135
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	357
Issue number	6
DOIs	https://doi.org/10.1002/adsc.201401163
Publication status	Published - 2015 Apr 13

Keywords

C-H activation
alkylation
enantioselectivity
indoles
iridium catalysts

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201401163

Cite this

@article{9ddfe44ac2334e2ca98464fa1c5a9c1d,

title = "Iridium-catalyzed intramolecular enantioselective c-h alkylation at the C-2 position of N-alkenylindoles",

abstract = "Intramolecular enantioselective alkylation of N-alkenylindoles proceeded via C-H bond cleavage at the C-2 position in the presence of a cationic iridium catalyst with a diphosphine ligand. Aroyl groups at the C-3 position of the indoles operated as effective directing groups, and chiral 1-substituted-2,3-dihydro-1H-pyrrolo[1,2-a]indoles were obtained in high yield with excellent ee.",

keywords = "C-H activation, alkylation, enantioselectivity, indoles, iridium catalysts",

author = "Takanori Shibata and Naoto Ryu and Hideaki Takano",

note = "Publisher Copyright: {\textcopyright} 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2015",

month = apr,

day = "13",

doi = "10.1002/adsc.201401163",

language = "English",

volume = "357",

pages = "1131--1135",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "6",

}

TY - JOUR

T1 - Iridium-catalyzed intramolecular enantioselective c-h alkylation at the C-2 position of N-alkenylindoles

AU - Shibata, Takanori

AU - Ryu, Naoto

AU - Takano, Hideaki

PY - 2015/4/13

Y1 - 2015/4/13

N2 - Intramolecular enantioselective alkylation of N-alkenylindoles proceeded via C-H bond cleavage at the C-2 position in the presence of a cationic iridium catalyst with a diphosphine ligand. Aroyl groups at the C-3 position of the indoles operated as effective directing groups, and chiral 1-substituted-2,3-dihydro-1H-pyrrolo[1,2-a]indoles were obtained in high yield with excellent ee.

AB - Intramolecular enantioselective alkylation of N-alkenylindoles proceeded via C-H bond cleavage at the C-2 position in the presence of a cationic iridium catalyst with a diphosphine ligand. Aroyl groups at the C-3 position of the indoles operated as effective directing groups, and chiral 1-substituted-2,3-dihydro-1H-pyrrolo[1,2-a]indoles were obtained in high yield with excellent ee.

KW - C-H activation

KW - alkylation

KW - enantioselectivity

KW - indoles

KW - iridium catalysts

UR - http://www.scopus.com/inward/record.url?scp=84926666387&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84926666387&partnerID=8YFLogxK

U2 - 10.1002/adsc.201401163

DO - 10.1002/adsc.201401163

M3 - Article

AN - SCOPUS:84926666387

SN - 1615-4150

VL - 357

SP - 1131

EP - 1135

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 6

ER -

Iridium-catalyzed intramolecular enantioselective c-h alkylation at the C-2 position of N-alkenylindoles

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this