CHEMO- AND STEREOSELECTIVE ADDITION OF DIORGANYLPHOSPHINE OXIDES TO α,β-ETHYLENIC ALDEHYDES

Abstract

Secondary phosphine oxides (R¹)₂P(O)H 1–3 react with α,β-ethylenic aldehydes R²CH=CHC(O)H 4–6 under mild conditions (THF, 22–42°C) to form chemo- and stereoselectively hydroxyethenylphosphine oxides (R¹)₂P(O)CH(OH)CH=CHR² (E) 7a–h in high yield.

Keywords:

• Addition
• α,β-ethylenic aldehydes
• secondary phosphine oxides

Financial support from the Ministry of Industry, Science and Technologies of Russian Federation (grant No. NSH-2241.2003.3) is acknowledged.

Notes

^a Isolated yields.

^b Yields calculated from the ³¹P NMR spectra of crude products.

^a Spectra of products 7a, b, d, e were taken in microlayer; spectra of products 7c, f, h were run in KBr.

^b A viscous liquid.

^c The spectrum was taken in vaseline oil.