Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Nonepimerizing Alkylation of H–P Species to Stereospecifically Generate P-Stereogenic Phosphine Oxides: A Shortcut to Bidentate Tertiary Phosphine Ligands

Nonepimerizing Alkylation of H–P Species to Stereospecifically Generate P-Stereogenic Phosphine Oxides: A Shortcut to Bidentate Tertiary Phosphine Ligands
Jing-Hong Wen, Shao-Zhen Nie, Chang-Qiu Zhao, Yun-Yao Cui, Hui Yan, Jing-Jing Ye, Zhong-Yang Zhou, Ji-Ping Wang
The secondary RP-(−)-menthyl alkylphosphine oxide was confirmed as configurationally stable toward base and was used in base-promoted alkylation, stereospecifically affording P-retained bis or functional tertiary phosphine oxides in excellent yields. The alkylated products were deoxygenated using oxalyl chloride followed by ZnCl2–NaBH4 to form P-inversed bidentate phosphine boranes in high stereoselectivities.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01413

DOI: 10.1021/acs.joc.7b01413

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