Issue 1, 2021

Regioselective and stereoselective cleavages of P–S/C–S bonds by lithium and the formation of P-stereogenic functional phosphine derivatives

Abstract

Various menthyl-containing phosphinothioates were prepared. Using these compounds, an unusual phosphorus-promoted cleavage of the C–S bond with lithium-naphthalene was examined. The C–S/P–S cleavages could be controlled by the amount of naphthalene and temperature applied. Also, the P–S cleavage was confirmed to retain the configuration about the P and this feature was used for achieving a stereospecific formation of the C–P bond.

Graphical abstract: Regioselective and stereoselective cleavages of P–S/C–S bonds by lithium and the formation of P-stereogenic functional phosphine derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
02 Aug 2020
Accepted
11 Oct 2020
First published
12 Oct 2020

Org. Chem. Front., 2021,8, 46-52

Regioselective and stereoselective cleavages of P–S/C–S bonds by lithium and the formation of P-stereogenic functional phosphine derivatives

X. Wang, Z. Li, Y. Zhang, B. Yan, H. Zheng, Q. Li and C. Zhao, Org. Chem. Front., 2021, 8, 46 DOI: 10.1039/D0QO00891E

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