Calcium(ii)-catalyzed [2+3] annulation of enynones: a sustainable approach to 9H-pyrrolo[1,2-a]indole frameworks

Ashok Kale; Shubham C. Rivonker; Jong Hyuk Kim; Jong Yeon Hwang; Yongseok Choi; Kyeong Lee

doi:10.1039/d5cc02204e

Calcium(ii)-catalyzed [2+3] annulation of enynones: a sustainable approach to 9H-pyrrolo[1,2-a]indole frameworks

Ashok Kale
, Shubham C. Rivonker
, Jong Hyuk Kim
, Jong Yeon Hwang
, Yongseok Choi
, Kyeong Lee

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

Abstract

A Ca(ii)-catalyzed, atom-economic, and regioselective [2+3] annulation reaction has been developed to synthesize 9H-pyrrolo[1,2-a]indoles by using easily accessible tryptamines and enynones. This protocol exhibits broad functional group tolerance; thus, 9H-pyrrolo[1,2-a]indole frameworks with diverse substitution patterns can be synthesized. The synthetic utility of this method is further demonstrated through its effectiveness in gram-scale preparations and versatile synthetic transformations.

Original language	English
Pages (from-to)	11689-11692
Number of pages	4
Journal	Chemical Communications
Volume	61
Issue number	62
DOIs	https://doi.org/10.1039/d5cc02204e
State	Published - 29 Jul 2025

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title = "Calcium(ii)-catalyzed [2+3] annulation of enynones: a sustainable approach to 9H-pyrrolo[1,2-a]indole frameworks",

abstract = "A Ca(ii)-catalyzed, atom-economic, and regioselective [2+3] annulation reaction has been developed to synthesize 9H-pyrrolo[1,2-a]indoles by using easily accessible tryptamines and enynones. This protocol exhibits broad functional group tolerance; thus, 9H-pyrrolo[1,2-a]indole frameworks with diverse substitution patterns can be synthesized. The synthetic utility of this method is further demonstrated through its effectiveness in gram-scale preparations and versatile synthetic transformations.",

author = "Ashok Kale and Rivonker, \{Shubham C.\} and Kim, \{Jong Hyuk\} and Hwang, \{Jong Yeon\} and Yongseok Choi and Kyeong Lee",

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doi = "10.1039/d5cc02204e",

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AU - Kale, Ashok

AU - Rivonker, Shubham C.

AU - Kim, Jong Hyuk

AU - Hwang, Jong Yeon

AU - Choi, Yongseok

AU - Lee, Kyeong

PY - 2025/7/29

Y1 - 2025/7/29

N2 - A Ca(ii)-catalyzed, atom-economic, and regioselective [2+3] annulation reaction has been developed to synthesize 9H-pyrrolo[1,2-a]indoles by using easily accessible tryptamines and enynones. This protocol exhibits broad functional group tolerance; thus, 9H-pyrrolo[1,2-a]indole frameworks with diverse substitution patterns can be synthesized. The synthetic utility of this method is further demonstrated through its effectiveness in gram-scale preparations and versatile synthetic transformations.

AB - A Ca(ii)-catalyzed, atom-economic, and regioselective [2+3] annulation reaction has been developed to synthesize 9H-pyrrolo[1,2-a]indoles by using easily accessible tryptamines and enynones. This protocol exhibits broad functional group tolerance; thus, 9H-pyrrolo[1,2-a]indole frameworks with diverse substitution patterns can be synthesized. The synthetic utility of this method is further demonstrated through its effectiveness in gram-scale preparations and versatile synthetic transformations.

UR - https://www.scopus.com/pages/publications/105009896052

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DO - 10.1039/d5cc02204e

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JO - Chemical Communications

JF - Chemical Communications

IS - 62

ER -

Calcium(ii)-catalyzed [2+3] annulation of enynones: a sustainable approach to 9H-pyrrolo[1,2-a]indole frameworks

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