Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes

James E. McGettigan; Joseph M. Ready

doi:10.1002/anie.202216961

Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes

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

Abstract

Alkenyl boronate complexes react with acylated quinolines and isoquinolines via 1,2-metalate rearrangement to give alkylated, dearomatized heterocycles in good yields, diastereoselectivities, and regioselectivities. This multi-component coupling is highly modular and can be used to access a wide scope of heterocyclic scaffolds. Chiral boronic esters made through this methodology possess high synthetic potential and can be transformed into various functional groups in one step without racemization.

Original language	English (US)
Article number	e202216961
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	16
DOIs	https://doi.org/10.1002/anie.202216961
State	Published - Apr 11 2023

Keywords

Alkenyl Boronate
Isoquinolines
Multicomponent Coupling
Quinolines

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.202216961

Cite this

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title = "Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes",

abstract = "Alkenyl boronate complexes react with acylated quinolines and isoquinolines via 1,2-metalate rearrangement to give alkylated, dearomatized heterocycles in good yields, diastereoselectivities, and regioselectivities. This multi-component coupling is highly modular and can be used to access a wide scope of heterocyclic scaffolds. Chiral boronic esters made through this methodology possess high synthetic potential and can be transformed into various functional groups in one step without racemization.",

keywords = "Alkenyl Boronate, Isoquinolines, Multicomponent Coupling, Quinolines",

author = "McGettigan, {James E.} and Ready, {Joseph M.}",

note = "Funding Information: Financial Support provided by the Welch Foundation (I‐1612) and NIH (RM1GM142002). X‐ray Crystallography performed by Dr. Vincent Lynch (UT Austin) and Dr. Allen Oliver (Notre Dame). We thank Dr. Feng Lin (UT Southwestern) for help with VT NMR experiments. Publisher Copyright: {\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

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doi = "10.1002/anie.202216961",

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T1 - Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes

AU - McGettigan, James E.

AU - Ready, Joseph M.

N1 - Funding Information: Financial Support provided by the Welch Foundation (I‐1612) and NIH (RM1GM142002). X‐ray Crystallography performed by Dr. Vincent Lynch (UT Austin) and Dr. Allen Oliver (Notre Dame). We thank Dr. Feng Lin (UT Southwestern) for help with VT NMR experiments. Publisher Copyright: © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

PY - 2023/4/11

Y1 - 2023/4/11

N2 - Alkenyl boronate complexes react with acylated quinolines and isoquinolines via 1,2-metalate rearrangement to give alkylated, dearomatized heterocycles in good yields, diastereoselectivities, and regioselectivities. This multi-component coupling is highly modular and can be used to access a wide scope of heterocyclic scaffolds. Chiral boronic esters made through this methodology possess high synthetic potential and can be transformed into various functional groups in one step without racemization.

AB - Alkenyl boronate complexes react with acylated quinolines and isoquinolines via 1,2-metalate rearrangement to give alkylated, dearomatized heterocycles in good yields, diastereoselectivities, and regioselectivities. This multi-component coupling is highly modular and can be used to access a wide scope of heterocyclic scaffolds. Chiral boronic esters made through this methodology possess high synthetic potential and can be transformed into various functional groups in one step without racemization.

KW - Alkenyl Boronate

KW - Isoquinolines

KW - Multicomponent Coupling

KW - Quinolines

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ER -

Diastereoselective Alkylation of Activated Nitrogen Heterocycles with Alkenyl Boronate Complexes

Abstract

Keywords

ASJC Scopus subject areas

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