4.6 Article

Synthesis of Chiral α-Substituted β-Aminophosphine Derivatives through Asymmetric Hydrophosphinylation Utilizing Secondary Phosphine Sulfides

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 17, Issue 24, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.202200989

Keywords

alpha-substituted beta-aminophosphines; asymmetric hydrophosphinylation; secondary phosphine sulfides; organocatalysis

Funding

  1. JSPS KAKENHI [19 K07002]

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This study presents an efficient organocatalytic method for the enantioselective hydrophosphinylation of various phosphine sulfides with aromatic and aliphatic nitroalkenes, resulting in chiral 13-nitrophosphine sulfides with high yields and enantioselectivities. Furthermore, the chiral beta-nitrophosphine sulfides can be easily converted into useful P, N-ligands and phosphine catalysts.
The organocatalytic enantioselective hydrophosphinylation of various secondary phosphine sulfides with aromatic and aliphatic nitroalkenes is presented in this study. The reaction produced chiral 13-nitrophosphine sulfides with excellent yields and enantioselectivities (up to 99% yield and 99% ee). Furthermore, the chiral beta-nitrophosphine sulfides can be easily converted into alpha-substituted beta-aminophosphine, which is a family of useful P, N-ligands and phosphine catalysts.

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