Diastereoselective C(sp3)-H acetoxylation of phosphoramidites.

Anirban Mondal; Vanda Dašková; Xiaobing Chen; Niklas O Thiel; Georgios Alachouzos; Ben L Feringa

doi:10.1039/d5cc00550g

Diastereoselective C(sp³)-H acetoxylation of phosphoramidites.

Anirban Mondal
, Vanda Dašková
, Xiaobing Chen
, Niklas O Thiel
, Georgios Alachouzos
, Ben L Feringa^*

^*Corresponding author for this work

Synthetic Organic Chemistry

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

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Abstract

Chiral phosphines are important ligands in asymmetric catalysis, yet their potential as directing groups for asymmetric C-H activation remains unexplored due to the oxidative nature of these reactions. We present a Pd-catalysed, P(III)-directed diastereoselective acetoxylation of phosphoramidites, with DFT calculations elucidating their unique reactivity and supporting the proposed reaction mechanism.

Original language	English
Article number	d5cc00550g
Pages (from-to)	6510-6513
Number of pages	4
Journal	Chemical communications (Cambridge, England)
Volume	61
Issue number	35
Early online date	7-Apr-2025
DOIs	https://doi.org/10.1039/d5cc00550g
Publication status	Published - 2-May-2025

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title = "Diastereoselective C(sp3)-H acetoxylation of phosphoramidites.",

abstract = "Chiral phosphines are important ligands in asymmetric catalysis, yet their potential as directing groups for asymmetric C-H activation remains unexplored due to the oxidative nature of these reactions. We present a Pd-catalysed, P(III)-directed diastereoselective acetoxylation of phosphoramidites, with DFT calculations elucidating their unique reactivity and supporting the proposed reaction mechanism.",

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AU - Mondal, Anirban

AU - Dašková, Vanda

AU - Chen, Xiaobing

AU - Thiel, Niklas O

AU - Alachouzos, Georgios

AU - Feringa, Ben L

PY - 2025/5/2

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N2 - Chiral phosphines are important ligands in asymmetric catalysis, yet their potential as directing groups for asymmetric C-H activation remains unexplored due to the oxidative nature of these reactions. We present a Pd-catalysed, P(III)-directed diastereoselective acetoxylation of phosphoramidites, with DFT calculations elucidating their unique reactivity and supporting the proposed reaction mechanism.

AB - Chiral phosphines are important ligands in asymmetric catalysis, yet their potential as directing groups for asymmetric C-H activation remains unexplored due to the oxidative nature of these reactions. We present a Pd-catalysed, P(III)-directed diastereoselective acetoxylation of phosphoramidites, with DFT calculations elucidating their unique reactivity and supporting the proposed reaction mechanism.

U2 - 10.1039/d5cc00550g

DO - 10.1039/d5cc00550g

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JF - Chemical communications (Cambridge, England)

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