210408-13-2Relevant articles and documents
Enantioselective desymmetrization of meso epoxides with anilines catalyzed by a niobium complex of a chiral multidentate binol derivative
Arai, Kenzo,Salter, Matthew M.,Yamashita, Yasuhiro,Kobayashi, Shu
, p. 955 - 957 (2007)
Molecular recognition in the desymmetrization of meso epoxides with anilines is displayed by a Lewis acid catalyst formed from niobium(V) methoxide and a novel tetradentate binol derivative. The catalyst has a remarkable ability to distinguish between dif
Synthesis of chiral ligands with multiple stereogenic centers and their application in titanium(iv)-catalyzed enantioselective desymmetrization of meso-epoxides
Kumar, Manish,Kureshy, Rukhsana I.,Ghosh, Debashis,Khan, Noor-UL H.,Abdi, Sayed H. R.,Bajaj, Hari C.
, p. 2336 - 2342 (2013/08/23)
New chiral ligands, (S,R,S)-1, (S,S,S)-1, (S,S,R)-1, (S,R,R)-1, (R,R,R)-1, (R,R,S)-1, (R,S,S)-1, (R,S,R)-1, (S,R,S)-2, (S,S)-3 and (R,S)-4 with diverse stereogenic centers arising from various diastereomeric combinations of aminoalcohol functionality with
Synthesis of enantiopure β-amino alcohols via AKR/ARO of epoxides using recyclable macrocyclic Cr(III) salen complexes
Kureshy, Rukhsana Ilays,Prathap, K. Jeya,Kumar, Manish,Bera, Prasanta Kumar,Khan, Noor-Ul Hasan,Abdi, Sayed Hasan Razi,Bajaj, Hari Chandra
supporting information; experimental part, p. 8300 - 8307 (2011/11/12)
A series of chiral macrocyclic Cr(III) salen complexes 1-8 were synthesized and characterized. These complexes were found to be highly active, regio-, diastereo-, and enantioselective catalysts in aminolytic kinetic resolution (AKR) of racemic trans-epoxides as well as asymmetric ring opening (ARO) of prochiral meso-epoxides with various anilines as nucleophiles at room temperature in 18-24 h. Excellent yields (>99% with respect to the nucleophile) with high enantioselectivity (ee, >99%) of chiral anti-β-amino alcohols was achieved with concomitant recovery of corresponding epoxides in high ee (up to >99%). The complex 1 also catalyzed the ARO of meso-epoxides to provide corresponding syn-β-amino alcohols in high yield (99%) and ee (up to 91%). Due to built-in basic sites in the catalyst, no external base (as an additive) was required to promote AKR and ARO reactions. The catalyst 1 was conveniently recycled several times with retention of its performance. The AKR of trans-stilbene oxide with aniline was successfully demonstrated at relatively higher scale (10 mmol) using the catalyst 1.
