85522-68-5Relevant academic research and scientific papers
Single or Synergistic Kinetic Resolutions of Chiral Allylalanes: Two Complementary Routes for the Asymmetric Synthesis of Syn Homoallylamines
Coffinet, Micha?l,Behr, Jean-Bernard,Jaroschik, Florian,Harakat, Dominique,Vasse, Jean-Luc
supporting information, p. 6728 - 6731 (2017/12/26)
Two strategies based on kinetic resolution(s) of chiral alanes and providing enantioenriched syn homoallylamines are reported. The first implies a single kinetic resolution of the alane using camphor; the second requires two sequential kinetic resolutions using the synergistic combination of (-)-camphor/(R)-tert-butylsulfinamide-derived imines. This syn selectivity, specific to the use of allyaluminum, opens the way to the preparation of valuable building blocks as illustrated by the synthesis of (+)-epilupinamine.
Steric influence of N-phosphorus-arylimines on the rhodium-catalyzed asymmetric arylation
Hao, Xinyu,Chen, Qian,Yamada, Ken-Ichi,Yamamoto, Yasutomo,Tomioka, Kiyoshi
scheme or table, p. 6469 - 6473 (2011/09/20)
Examination of the rhodium-catalyzed asymmetric arylation of benzaldehyde-imines bearing ethoxy, isopropoxy, phenyl, cyclohexyl, 3,5-xylyl, and 2,4,6-mesityl N-phosphorus activating/protecting groups revealed that bulky N-phosphorus groups retarded the arylation and at the same time prevented the competitive hydrolysis of an imine. Although the level of enantioselectivity was dependent favorably on the bulkiness ranging from 88% ee to 53% ee, the reactivity was drastically decreased along with bulkiness ranging from 95% to 3%.
PHOSPHORUS ANALOGUES OF AMINO ACIDS AND PEPTIDES XII. REACTION OF SODIUM DIETHYL PHOSPHITE WITH AROMATIC ALDAZINES AND HYDRAZONES
Topolski, M.,Rachon, J.
, p. 97 - 110 (2007/10/02)
The mechanism of the reaction of sodium diethyl phosphite with aromatic aldazines has been investigated.The initially formed monoaddition product (4) reacts with the excess of phosphorus reagent prior to the conceivable addition of diethyl phosphite to the C=N double bond.Cleavage of the N-N single bond is initiated by Single Electron Transfer from phosphite anion to the conjugated N=CH-Ph bond system.The scope of the reaction can be extended to other aromatic hydrazones.There is strong evidence to support the operation of a non-chain SET mechanism.
