Aminoselenenylation of alkenes: syntheses of β-phenylseleno carbamates and β-phenylseleno cyanamides

New Developments with Chiral Electrophilic Selenium Reagents

“…Nitriles have been used as versatile nucleophiles in this reaction which can be converted into the corresponding amides [88,89,90]. But also other nitrogencontaining nucleophiles such as carbamates [91] or tosylamides [92] can be employed. Azidoselenenylations have been investigated as well, with the azide ion serving as a nitrogen nucleophile [93,94,95].…”

N-Phenylselenophthalimide

“…31b Similarly, 2-cholestene produced vicinal phenylseleno carbamates and cyanamides via eqs 19 and 20, respectively. 33 The combination of NPSP with azidotrimethylsilane provides a useful reagent for the 1,2-addition of phenylseleno and azide groups to alkenes, 34 as in the example shown in eq 21 …”

“…In a variation of eq 4, 1,4-cyclooctadiene reacted with NPSP and cyanamide to afford aza-bridged regioisomers (eq 22). 33 A catalytic variation of the usual lactonization of unsaturated carboxylic acids (as in eq 8) was observed when NPSP was used in the presence of the stoichiometric oxidant ammonium persulfate. This resulted in selenoxide elimination of the initially cyclized product and generated other electrophilic selenium species that continued the cyclization process (eq 23).…”