Diselenophosphinates of lupinine or anabasine via a new three-component reaction of secondary phosphines, elemental selenium, and amines

✍ Scribed by Nina K. Gusarova; Alexander V. Artem’ev; Svetlana F. Malysheva; Sergei V. Fedorov; Olga N. Kazheva; Grigorii G. Alexandrov; Oleg A. Dyachenko; Boris A. Trofimov

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 406 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.01.116

✦ Synopsis

Secondary phosphines, elemental selenium, and the natural alkaloids, lupinine and anabasine, interact in a three-component-type reaction under mild conditions (70 °C, 1-1.5 h, EtOH) without the formation of any by-products to give diselenophosphinates of the above-mentioned alkaloids (in almost quantitative yields) with the retention of their intrinsic optical activity. Thus, the developed synthesis represents an atom-economic route to new selenophosphorus derivatives of alkaloids.