295795-88-9Relevant academic research and scientific papers
Chiral o-methoxyaryldiazaphosphonamides - A new class of efficient Lewis bases in the catalytic asymmetric ring opening of cyclooctene oxide with silicon tetrachloride
Reymond, Sebastien,Legrand, Olivier,Brunel, Jean Michel,Buono, Gerard
, p. 2819 - 2823 (2001)
The synthesis of a new class of chiral o-methoxydiazaphosphonamides (as Lewis bases) has been investigated, together with their use as catalysts in the asymmetric ring opening (ARO) of cyclooctene oxide with silicon tetrachloride. Enantiomeric excesses varying from 6 to 99% ee were observed, depending on the nature of the catalyst examined. On the basis of experimental considerations, a mechanistic rationale involving hexacoordinate silicon species has been proposed.
New chiral o-hydroxyphenyl diazaphospholidine oxide. Catalytic application in asymmetric addition of diethylzinc to aromatic aldehydes
Brunel, Jean-Michel,Constantieux, Thierry,Legrand, Olivier,Buono, Gerard
, p. 2961 - 2964 (2007/10/03)
Synthesis of diastereomerically pure o-hydroxyphenyl diazaphospholidine oxide 2 was achieved from a chiral diamine derived from (S)-proline. This new compound has been tested as catalyst in the asymmetric addition of diethylzinc to aromatic aldehydes. Corresponding sec-alcohols were obtained in high yields (up to 90%) with enantiomeric excesses varying from 15 to >99%. The influence of the solvent and also the important relation existing between the nature of the aldehydes and the enantioselectivity have been investigated.
