Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides

Xiaobing Chen; Damián Padin Santos; Lotte Stindt; Ben L. Feringa

doi:10.1002/anie.202307450

Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides

Xiaobing Chen, Damián Padin Santos^*, Lotte Stindt, Ben L. Feringa^*

^*Corresponding author for this work

Synthetic Organic Chemistry

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

12 Citations (Scopus)

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Abstract

P-stereogenic compounds are widely used as ligands in asymmetric catalysis and are present in a myriad of bioactive compounds and pharmaceuticals. Yet, their stereocontrolled preparation remains challenging. Herein, we report a novel strategy towards versatile chiral-at-P alkenylphosphonamidates through a one-pot Ni-catalyzed C-P coupling/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. Remarkably, a chemo- and diastereodivergent behavior was observed upon subtle changes in the reaction conditions. Additionally, selective derivatizations of chiral alkenylphosphonamidates demonstrate their versatility as building blocks for the synthesis of structurally diverse P-stereogenic compounds.

Original language	English
Article number	e202307450
Number of pages	8
Journal	Angewandte Chemie (International ed. in English)
Volume	62
Issue number	33
Early online date	6-Jul-2023
DOIs	https://doi.org/10.1002/anie.202307450
Publication status	Published - 14-Aug-2023

Keywords

Asymmetric Synthesis
Chiral Auxiliaries
Cross-Coupling
Nickel
Phosphorus

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10.1002/anie.202307450Licence: CC BY

Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C−P Coupling of Phosphoramidites and Alkenyl HalidesFinal publisher's version, 5.88 MBLicence: CC BY

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CCDC 2265258: Experimental Crystal Structure Determination
Chen, X. (Contributor), Padín, D. (Contributor), Stindt, L. (Contributor) & Feringa, B. L. (Contributor), Cambridge Crystallographic Data Centre, 24-May-2023
DOI: 10.5517/ccdc.csd.cc2g15vk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2g15vk&sid=DataCite
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oLife Fellowship Programme
Roos, W. (PI), van der Tak, F. (PI), Zijlstra, W. (PI), Dobos, V. (Postdoc), Heinen, L. (Postdoc), Thangaratnarajah, C. (Postdoc), Hoekzema, M. (Postdoc), Blokhuis, A. (Postdoc), Mascotti, L. (Postdoc), Padin Santos, D. (Postdoc), Chopra, A. (Postdoc), Obermaier, S. (Postdoc), Driver, M. (Postdoc), Moreira Goulart, M. (Postdoc), Sasidharan, S. (Postdoc), Samar Mahapatra, S. (Postdoc), Zylstra, A. (Postdoc), Geiger, Y. (Postdoc), Llopis Lorente, A. (Postdoc), Aschmann, D. (Postdoc) & Kulala Vittala, S. (Postdoc)
01/04/2019 → 31/03/2024
Project: Research

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title = "Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides",

abstract = "P-stereogenic compounds are widely used as ligands in asymmetric catalysis and are present in a myriad of bioactive compounds and pharmaceuticals. Yet, their stereocontrolled preparation remains challenging. Herein, we report a novel strategy towards versatile chiral-at-P alkenylphosphonamidates through a one-pot Ni-catalyzed C-P coupling/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. Remarkably, a chemo- and diastereodivergent behavior was observed upon subtle changes in the reaction conditions. Additionally, selective derivatizations of chiral alkenylphosphonamidates demonstrate their versatility as building blocks for the synthesis of structurally diverse P-stereogenic compounds.",

keywords = "Asymmetric Synthesis, Chiral Auxiliaries, Cross-Coupling, Nickel, Phosphorus",

author = "Xiaobing Chen and {Padin Santos}, Dami{\'a}n and Lotte Stindt and Feringa, {Ben L.}",

note = "{\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.",

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volume = "62",

journal = "Angewandte Chemie (International ed. in English)",

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Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides. / Chen, Xiaobing; Padin Santos, Damián; Stindt, Lotte et al.
In: Angewandte Chemie (International ed. in English), Vol. 62, No. 33, e202307450, 14.08.2023.

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

TY - JOUR

T1 - Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides

AU - Chen, Xiaobing

AU - Padin Santos, Damián

AU - Stindt, Lotte

AU - Feringa, Ben L.

PY - 2023/8/14

Y1 - 2023/8/14

N2 - P-stereogenic compounds are widely used as ligands in asymmetric catalysis and are present in a myriad of bioactive compounds and pharmaceuticals. Yet, their stereocontrolled preparation remains challenging. Herein, we report a novel strategy towards versatile chiral-at-P alkenylphosphonamidates through a one-pot Ni-catalyzed C-P coupling/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. Remarkably, a chemo- and diastereodivergent behavior was observed upon subtle changes in the reaction conditions. Additionally, selective derivatizations of chiral alkenylphosphonamidates demonstrate their versatility as building blocks for the synthesis of structurally diverse P-stereogenic compounds.

AB - P-stereogenic compounds are widely used as ligands in asymmetric catalysis and are present in a myriad of bioactive compounds and pharmaceuticals. Yet, their stereocontrolled preparation remains challenging. Herein, we report a novel strategy towards versatile chiral-at-P alkenylphosphonamidates through a one-pot Ni-catalyzed C-P coupling/diastereoselective hydrolysis of readily available phosphoramidites and alkenyl halides. Remarkably, a chemo- and diastereodivergent behavior was observed upon subtle changes in the reaction conditions. Additionally, selective derivatizations of chiral alkenylphosphonamidates demonstrate their versatility as building blocks for the synthesis of structurally diverse P-stereogenic compounds.

KW - Asymmetric Synthesis

KW - Chiral Auxiliaries

KW - Cross-Coupling

KW - Nickel

KW - Phosphorus

U2 - 10.1002/anie.202307450

DO - 10.1002/anie.202307450

M3 - Article

C2 - 37345853

SN - 1433-7851

VL - 62

JO - Angewandte Chemie (International ed. in English)

JF - Angewandte Chemie (International ed. in English)

IS - 33

M1 - e202307450

ER -

Asymmetric Synthesis of Chiral-at-P Alkenylphosphonamidates through Nickel-Catalyzed C-P Coupling of Phosphoramidites and Alkenyl Halides

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Keywords

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Datasets

CCDC 2265258: Experimental Crystal Structure Determination

Projects

oLife Fellowship Programme

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