207573-10-2Relevant academic research and scientific papers
Asymmetric electrophilic methoxyselenenylations and cyclizations with 3- camphorseleno derivatives
Back, Thomas G.,Dyck, Brian P.,Nan, Siqiao
, p. 3191 - 3208 (1999)
A series of novel 3-camphor-based diselenides, differing in substitution at C-2, was prepared. The corresponding allyl selenides were used as protecting groups for the diselenide moieties in several subsequent transformations. The diastereoselective methoxyselenenylation of alkenes was achieved with methanolic selenenyl triflates derived from the camphor diselenides, of which the 2-keto analogue proved the most effective. Diastereoselective electrophilic cyclizations of unsaturated alcohols, carboxylic acids and amides were most effectively performed with the corresponding selenenyl chloride, containing a spiro-oxazolidinone moiety at C-2 of the camphor residue. The absolute configurations of several products were determined by reductive deselenization.
Asymmetric selenomethoxylation of alkenes with camphorselenenyl sulfate
Tiecco, Marcello,Testaferri, Lorenzo,Santi, Claudio,Marini, Francesca,Bagnoli, Luana,Temperini, Andrea
, p. 2809 - 2812 (2007/10/03)
By reaction with ammonium persulfate the easily available diselenide derived from (1R)-(+)-camphor was converted into the camphorselenenyl sulfate. This chiral electrophilic selenium reagent reacted at room temperature with alkenes in the presence of methanol to afford selenomethoxylated adducts in good yields and with moderate to good facial selectivity. The two diastereomeric addition products could be separated in most cases.
Asymmetric methoxyselenenylations with camphor-based selenium electrophiles
Back, Thomas G.,Nan, Siqiao
, p. 3123 - 3124 (2007/10/03)
The asymmetric methoxyselenenylation of olefins was achieved with a series of camphor-based selenenyl triflates, of which the readily available 2-oxo analog 2a proved the most effective.
