α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

Nico Seling; Masakazu Atobe; Kevin Kasten; James D Firth; Peter B Karadakov; Frederick W Goldberg; Peter O'Brien

doi:10.1002/anie.202314423

α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

Nico Seling, Masakazu Atobe, Kevin Kasten, James D Firth, Peter B Karadakov, Frederick W Goldberg, Peter O'Brien

Chemistry

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

Abstract

A general and straightforward procedure for the lithiation / trapping of cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyran and a thiomorpholine is described. Trapping with a wide range of electrophiles is demonstrated, leading to more than 50 diverse α-substituted saturated sulfur heterocycles. The methodology provides access to a range of α-substituted cyclic sulfides that are not easily synthesised by the currently available methods.

Original language	English
Article number	e202314423
Number of pages	7
Journal	Angewandte Chemie International Edition
Early online date	7 Dec 2023
DOIs	https://doi.org/10.1002/anie.202314423
Publication status	E-pub ahead of print - 7 Dec 2023

Bibliographical note

Keywords

Organolithium, cyclic sulfides, α-functionalization

Access to Document

10.1002/anie.202314423Licence: CC BY

Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping
© 2023 The Authors.
Final published version, 7.7 MBLicence: CC BY

Stereospecific Csp3-Csp2 Cross-Coupling of Heterocyclic Alkyl Borona_A Transformative Disconnection for Drug Discovery
O'Brien, P. A. (Principal investigator) & Fairlamb, I. J. S. (Co-investigator)
EPSRC
1/05/21 → 30/04/23
Project: Research project (funded) › Research
Modular Approach for Elaborating Fragments to 3-D Lead Compounds for Drug Discovery: Bifunctional 3-D Building Blocks with Distinct 3-D Vectors
O'Brien, P. A. (Principal investigator)
THE ROYAL SOCIETY
1/07/19 → 30/06/23
Project: Research project (funded) › Research
C-H Functionalisation of Cyclic Ethers: New Routes to 3-D Fragments, Scaffolds and Pharmaceuticals
O'Brien, P. A. (Principal investigator) & Karadakov, P. B. (Co-investigator)
EPSRC
16/01/17 → 30/09/20
Project: Research project (funded) › Research

Dataset for sulfur lithiation paper
O'Brien, P. A. (Creator), Firth, J. (Contributor), Kasten, K. (Contributor), Seling, N. (Contributor), Atobe, M. (Contributor) & Karadakov, P. B. (Supervisor), University of York, 8 Jan 2024
DOI: 10.15124/54fed6f9-e4a1-4cc5-b10b-aeb492da4043
Dataset

Cite this

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title = "α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping",

abstract = "A general and straightforward procedure for the lithiation / trapping of cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyran and a thiomorpholine is described. Trapping with a wide range of electrophiles is demonstrated, leading to more than 50 diverse α-substituted saturated sulfur heterocycles. The methodology provides access to a range of α-substituted cyclic sulfides that are not easily synthesised by the currently available methods.",

keywords = "Organolithium, cyclic sulfides, α-functionalization",

author = "Nico Seling and Masakazu Atobe and Kevin Kasten and Firth, {James D} and Karadakov, {Peter B} and Goldberg, {Frederick W} and Peter O'Brien",

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doi = "10.1002/anie.202314423",

language = "English",

journal = "Angewandte Chemie International Edition",

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T1 - α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

AU - Seling, Nico

AU - Atobe, Masakazu

AU - Kasten, Kevin

AU - Firth, James D

AU - Karadakov, Peter B

AU - Goldberg, Frederick W

AU - O'Brien, Peter

PY - 2023/12/7

Y1 - 2023/12/7

N2 - A general and straightforward procedure for the lithiation / trapping of cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyran and a thiomorpholine is described. Trapping with a wide range of electrophiles is demonstrated, leading to more than 50 diverse α-substituted saturated sulfur heterocycles. The methodology provides access to a range of α-substituted cyclic sulfides that are not easily synthesised by the currently available methods.

AB - A general and straightforward procedure for the lithiation / trapping of cyclic sulfides such as tetrahydrothiophene, tetrahydrothiopyran and a thiomorpholine is described. Trapping with a wide range of electrophiles is demonstrated, leading to more than 50 diverse α-substituted saturated sulfur heterocycles. The methodology provides access to a range of α-substituted cyclic sulfides that are not easily synthesised by the currently available methods.

KW - Organolithium, cyclic sulfides, α-functionalization

U2 - 10.1002/anie.202314423

DO - 10.1002/anie.202314423

M3 - Article

C2 - 37984884

SN - 1433-7851

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

M1 - e202314423

ER -

α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping

Abstract

Bibliographical note

Keywords

Access to Document

Projects

Stereospecific Csp3-Csp2 Cross-Coupling of Heterocyclic Alkyl Borona_A Transformative Disconnection for Drug Discovery

Modular Approach for Elaborating Fragments to 3-D Lead Compounds for Drug Discovery: Bifunctional 3-D Building Blocks with Distinct 3-D Vectors

C-H Functionalisation of Cyclic Ethers: New Routes to 3-D Fragments, Scaffolds and Pharmaceuticals

Datasets

Dataset for sulfur lithiation paper

Cite this