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2021-06-03

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/189775

BOM-phosphinite as an electrophilic P-stereogenic transfer reagent for the synthesis of bulky phosphines. Synthesis of tert-butyl(3,5-di-tert-butylphenyl)BisP*

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https://doi.org/10.1021/acs.orglett.1c01522

Abstract

BOM-tert-butylmethylphosphinite borane is an efficient electrophilic P-stereogenic transfer reagent for the synthesis of bulky tertiary phosphines. The novel methodology relies on a one-pot deprotection/substitution process. The substitution of the trivalent phosphinite takes place with high stereospecificity and provides the products with inversion of configuration at the phosphorus atom. The potential of the methodology is demonstrated with the synthesis of a wide scope of tertiary phoshines in excellent enantiomeric excess. Finally the methodology was applied to the synthesis of bulky P-stereogenic BisP* ligand analog.

Subject

Fòsfor, Lligands, Química analítica

Subject (English)

Phosphorus, Ligands, Analytical chemistry

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Articles publicats en revistes (Química Inorgànica i Orgànica)
Articles publicats en revistes (Institut de Recerca Biomèdica (IRB Barcelona))

Citation

ROJO, Pep, RIERA I ESCALÉ, Antoni and VERDAGUER I ESPAULELLA, Xavier. BOM-phosphinite as an electrophilic P-stereogenic transfer reagent for the synthesis of bulky phosphines. Synthesis of tert-butyl(3,5-di-tert-butylphenyl)BisP*. Organic Letters. 2021. Vol. 23, num. 12, pags. 4802-4806. ISSN 1523-7060. [consulted: 10 of August of 2026]. Available at: https://hdl.handle.net/2445/189775

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