Samarium iodides catalyzed meso-epoxides ring opening by aromatic amines

Facile Enantioselective Ring‐Opening Reaction of meso Epoxides with Anilines Using (S)‐(–)‐BINOL‐Ti Complex as a Catalyst

“…[21] However, until now, this area has been scarcely studied. [15] Nevertheless, various lanthanides [21,[22][23][24][25] with (R)/(S)-BINOL, Cr(Salen) [26] and Sc(bipyridine) [27] have been employed as catalysts for ringopening of meso epoxide with alkyl/arylamines to generate β-amino alcohols. Herein, we report the opening of mesostilbene oxide and cyclohexene oxide with aniline and substituted anilines, catalyzed by the recoverable (S)-BINOL-Ti complex to get enantio-enriched syn-β-amino alcohols and trans-β-amino alcohols in high yield (up to 95 %) with 78 % enantiomeric excess at ambient temperature.…”

Crystal structure of (1S,2R,4S)-1-((phenylamino)methyl)- 4-(prop-1-en-2-yl)cyclohexane-1,2-diol), C16H23NO2

“…Different approaches to obtain aminodiol derivatives have been developed [11][12][13]. Aminolysis of 1,2-epoxides represents one of the valuable pathway to produce commercially important aminoalcohols and aminodiols from olefins [14][15][16]. The absolute configuration has been assigned by reference to unchanging the chiral centres in the synthetic procedure.…”

Dimeric & Polymeric Chiral Schiff Base Complexes and Supported BINOL Complexes as Potential Recyclable Catalysts in Asymmetric Kinetic Resolution and C–C Bond Formation Reactions

“…b-Amino alcohols can also be prepared by the asymmetric ring opening (ARO) reaction of readily accessible meso epoxides with the desired amine. Indeed, some simple and multifunctional b-amino alcohols have been obtained with the AKR strategy by using chiral BINOL [12][13][14][15][16], salen [17,18], bipyridine [19][20][21][22][23][24][25] and proline-N,N-dioxide based metal complexes as catalysts [26]. However, none of these systems demonstrated the recyclability of the precious chiral catalyst.…”

“…Another important class of ligand used in various asymmetric organic transformations is BINOL. However, its use in epoxide ring opening reactions is limited and that too under homogeneous condition with no catalyst recycling data available [12][13][14][15][16]. In our laboratory [30] we used (S)-(-)-BINOL-Ti complexes 12-15 as recyclable catalysts in the enantioselective ring-opening reaction of meso stilbene oxide and cyclohexene oxide with anilines ( Fig.…”