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Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones. / Bowen, Eleanor; Laidlaw, Gillian; Atkinson, Bethany et al.
In: The Journal of Organic Chemistry, 05.08.2022, p. 10256–10276.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Bowen, E, Laidlaw, G, Atkinson, B, McArdle-Ismaguilov, T & Franckevicius, V 2022, 'Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones', The Journal of Organic Chemistry, pp. 10256–10276. https://doi.org/10.1021/acs.joc.2c01240

APA

Bowen, E., Laidlaw, G., Atkinson, B., McArdle-Ismaguilov, T., & Franckevicius, V. (2022). Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones. The Journal of Organic Chemistry, 10256–10276. https://doi.org/10.1021/acs.joc.2c01240

Vancouver

Bowen E, Laidlaw G, Atkinson B, McArdle-Ismaguilov T, Franckevicius V. Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones. The Journal of Organic Chemistry. 2022 Aug 5;10256–10276. Epub 2022 Jul 8. doi: 10.1021/acs.joc.2c01240

Author

Bowen, Eleanor ; Laidlaw, Gillian ; Atkinson, Bethany et al. / Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones. In: The Journal of Organic Chemistry. 2022 ; pp. 10256–10276.

Bibtex

@article{b53f7e86ef9847b5bb0ba8d4fd7ff9bb,
title = "Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones",
abstract = "As saturated heterocyclic building blocks become increasingly popular in medicinal chemistry and drug discovery programs, expansion of the synthetic toolkit to novel stereofunctionalized heterocycles is a priority. Herein, we report the development of a palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction to access a broad range of enantioenriched α-difunctionalized 5- and 6-membered sulfones from easily accessible racemic starting materials. The allylic alkylation step was found to occur with high levels of enantioselectivity as a result of a palladium-mediated dynamic kinetic resolution of E/Z enolate intermediates. This methodology paves the way to hitherto unexplored stereodefined cyclic sulfones for medicinal chemistry applications.",
author = "Eleanor Bowen and Gillian Laidlaw and Bethany Atkinson and Timur McArdle-Ismaguilov and Vilius Franckevicius",
year = "2022",
month = aug,
day = "5",
doi = "10.1021/acs.joc.2c01240",
language = "English",
pages = "10256–10276",
journal = "The Journal of Organic Chemistry",

}

RIS

TY - JOUR

T1 - Catalytic Enantioselective Synthesis of α‐Difunctionalized Cyclic Sulfones

AU - Bowen, Eleanor

AU - Laidlaw, Gillian

AU - Atkinson, Bethany

AU - McArdle-Ismaguilov, Timur

AU - Franckevicius, Vilius

PY - 2022/8/5

Y1 - 2022/8/5

N2 - As saturated heterocyclic building blocks become increasingly popular in medicinal chemistry and drug discovery programs, expansion of the synthetic toolkit to novel stereofunctionalized heterocycles is a priority. Herein, we report the development of a palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction to access a broad range of enantioenriched α-difunctionalized 5- and 6-membered sulfones from easily accessible racemic starting materials. The allylic alkylation step was found to occur with high levels of enantioselectivity as a result of a palladium-mediated dynamic kinetic resolution of E/Z enolate intermediates. This methodology paves the way to hitherto unexplored stereodefined cyclic sulfones for medicinal chemistry applications.

AB - As saturated heterocyclic building blocks become increasingly popular in medicinal chemistry and drug discovery programs, expansion of the synthetic toolkit to novel stereofunctionalized heterocycles is a priority. Herein, we report the development of a palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction to access a broad range of enantioenriched α-difunctionalized 5- and 6-membered sulfones from easily accessible racemic starting materials. The allylic alkylation step was found to occur with high levels of enantioselectivity as a result of a palladium-mediated dynamic kinetic resolution of E/Z enolate intermediates. This methodology paves the way to hitherto unexplored stereodefined cyclic sulfones for medicinal chemistry applications.

U2 - 10.1021/acs.joc.2c01240

DO - 10.1021/acs.joc.2c01240

M3 - Journal article

SP - 10256

EP - 10276

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

ER -