Ir-Catalyzed Enantioselective Formal C-H Conjugate Addition of Pyrrole and Indoles to α,β-Unsaturated Carbonyl Compounds

Takanori Shibata; Mio Sasaki; Masafumi Kojima; Mamoru Ito

doi:10.1021/acs.orglett.1c03375

Ir-Catalyzed Enantioselective Formal C-H Conjugate Addition of Pyrrole and Indoles to α,β-Unsaturated Carbonyl Compounds

Takanori Shibata^*, Mio Sasaki, Masafumi Kojima, Mamoru Ito

^*Corresponding author for this work

School of Advanced Science and Engineering

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

9 Citations (Scopus)

Abstract

The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with α,β-unsaturated carbonyl compounds such as crotonates proceeded with high enantioselectivity. The obtained chirally functionalized pyrroles and indoles are formal C-H conjugate adducts. The reaction mechanism was studied by deuterium labeling experiments.

Original language	English
Pages (from-to)	9078-9082
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	23
DOIs	https://doi.org/10.1021/acs.orglett.1c03375
Publication status	Published - 2021 Dec 3

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c03375

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abstract = "The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with α,β-unsaturated carbonyl compounds such as crotonates proceeded with high enantioselectivity. The obtained chirally functionalized pyrroles and indoles are formal C-H conjugate adducts. The reaction mechanism was studied by deuterium labeling experiments. ",

author = "Takanori Shibata and Mio Sasaki and Masafumi Kojima and Mamoru Ito",

note = "Funding Information: This work was supported by Waseda University Grant for Special Research Projects. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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AU - Shibata, Takanori

AU - Sasaki, Mio

AU - Kojima, Masafumi

AU - Ito, Mamoru

PY - 2021/12/3

Y1 - 2021/12/3

N2 - The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with α,β-unsaturated carbonyl compounds such as crotonates proceeded with high enantioselectivity. The obtained chirally functionalized pyrroles and indoles are formal C-H conjugate adducts. The reaction mechanism was studied by deuterium labeling experiments.

AB - The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with α,β-unsaturated carbonyl compounds such as crotonates proceeded with high enantioselectivity. The obtained chirally functionalized pyrroles and indoles are formal C-H conjugate adducts. The reaction mechanism was studied by deuterium labeling experiments.

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Ir-Catalyzed Enantioselective Formal C-H Conjugate Addition of Pyrrole and Indoles to α,β-Unsaturated Carbonyl Compounds

Abstract

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