Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 3, Pages 1672-1688Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502623g
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Funding
- Polish Ministry of Science and Higher Education [N N204 111 035]
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A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphineboranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O center dot center dot center dot B complexation directed by proximal alpha- or beta-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.
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