The stereoselective conversion of epimerized alkoxyl phosphine–borane to <i>P,C, axial</i>-stereogenic tertiary phosphine <i>via</i> cleavage of P–O bond

Zhai, De-Hua; Yan, Bing-Xia; Li, Zhancai; Lin, Zhu; Li, Qiang; Wang, Yan-Lan; Zheng, Hang; Zhao, Chang‐Qiu

doi:10.1039/d2ob00351a

Org. Biomol. Chem.

2022

DOI: 10.1039/d2ob00351a

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The stereoselective conversion of epimerized alkoxyl phosphine–borane to P,C, axial-stereogenic tertiary phosphine via cleavage of P–O bond

De-Hua Zhai

Bing-Xia Yan

Zhancai Li

et al.

Abstract: The P-O bond of epimerized alkoxyl phosphine-borane was cleaved by naphthalene-lithium, to form two diastereomers of P-anions in a ratio of 86:14, which was converted to secondary phosphine-borane via acidification,...

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2024

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Cited by 2 publications

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N‐Heterocyclic Carbene Enabled Copper Catalyzed Asymmetric Synthesis of Pyrimidinyl Phosphine with both Axial and P‐Stereogenicity

Cui,

Zhang,

Huang

et al. 2024

Angewandte Chemie

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P‐stereogenic phosphines, renowned for their utility as ligands and catalysts, have been instrumental in the field of asymmetric catalysis. However, the catalytic asymmetric synthesis of chiral ligands possessing both axial and phosphine chirality remains a significant challenge. Here, we present the successful demonstration of a Cu‐catalyzed asymmetric C‐P construction using in situ generated secondary phosphine and heteroaryl chloride. By introducing a chiral NHC ligand and an achiral diphosphine auxiliary ligand, we effectively alleviated the poisoning effect caused by phosphine(III) compounds and suppressed the nonenantioselective background reaction. The reaction exhibited excellent enantioselectivity, with up to 96% ee, and good diastereoselectivity, with up to 14:1 dr, when employing less sterically hindered secondary phosphines. This particular substrate poses a significant challenge due to its strong poisoning effect in copper catalysis.

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N‐Heterocyclic Carbene Enabled Copper Catalyzed Asymmetric Synthesis of Pyrimidinyl Phosphine with both Axial and P‐Stereogenicity

Cui,

Zhang,

Huang

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

N‐Heterocyclic Carbene Enabled Copper Catalyzed Asymmetric Synthesis of Pyrimidinyl Phosphine with both Axial and P‐Stereogenicity

Cui,

Zhang,

Huang

et al. 2024

Angew Chem Int Ed

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show abstract

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The stereoselective conversion of epimerized alkoxyl phosphine–borane to P,C, axial-stereogenic tertiary phosphine via cleavage of P–O bond

Abstract: The P-O bond of epimerized alkoxyl phosphine-borane was cleaved by naphthalene-lithium, to form two diastereomers of P-anions in a ratio of 86:14, which was converted to secondary phosphine-borane via acidification,...

Cited by 2 publications

References 59 publications

N‐Heterocyclic Carbene Enabled Copper Catalyzed Asymmetric Synthesis of Pyrimidinyl Phosphine with both Axial and P‐Stereogenicity

N‐Heterocyclic Carbene Enabled Copper Catalyzed Asymmetric Synthesis of Pyrimidinyl Phosphine with both Axial and P‐Stereogenicity

N‐Heterocyclic Carbene Enabled Copper Catalyzed Asymmetric Synthesis of Pyrimidinyl Phosphine with both Axial and P‐Stereogenicity

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