1517-67-5Relevant articles and documents
Mosher,Loeffler
, p. 4959 (1956)
Synthetic applicability and in situ recycling of a B-methoxy oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol
Gilmore, Nathan J.,Jones, Simon,Muldowney, Mark P.
, p. 2805 - 2808 (2004)
A procedure is described that greatly simplifies the use of an oxazaborolidine catalyst derived from (1R,2S) cis-1-amino-indan-2-ol. This B-OMe catalyst has been employed in the asymmetric reduction of a number of structurally diverse prochiral ketones, in particular the reduction of α-amino acetophenone and its derivatives. A method for reducing the effective catalyst loading by "in situ recycling" is also presented.
Asymmetric Reduction of Ketones with B-(cis-10-Pinanyl)-9-borabicyclononane. Observation of a Change in Enantioselection between Similar Organoborane and Organoaluminium Reagents
Midland, Mark M.,McLoughlin, Jim I.
, p. 4101 - 4102 (1984)
The title reagent reduces prochiral ketones of moderate steric bulk in modest to good enantiomeric excesses of the S alcohols.The absolute configuration is the opposite of that obtained with a similar organoaluminium reagent.
Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones
Zhang, Lin,Zhang, Ling,Chen, Qian,Li, Linlin,Jiang, Jian,Sun, Hao,Zhao, Chong,Yang, Yuanyong,Li, Chun
supporting information, p. 415 - 419 (2022/01/12)
Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0-99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.
Chiral Imidazo[1,5- a]pyridine-Oxazolines: A Versatile Family of NHC Ligands for the Highly Enantioselective Hydrosilylation of Ketones
Chinna Ayya Swamy,Varenikov, Andrii,Ruiter, Graham De
supporting information, p. 247 - 257 (2020/02/04)
Herein we report the synthesis and application of a versatile class of N-heterocyclic carbene ligands based on an imidazo[1,5-a]pyridine-3-ylidine backbone that is fused to a chiral oxazoline auxiliary. The key step in the synthesis of these ligands involves the installation of the oxazoline functionality via a microwave-assisted condensation of a cyano-azolium salt with a wide variety of 2-amino alcohols. The resulting chiral bidentate NHC-oxazoline ligands form stable complexes with rhodium(I) that are efficient catalysts for the enantioselective hydrosilylation of structurally diverse ketones. The corresponding secondary alcohols are isolated in good yields (typically >90%) with good to excellent enantioselectivities (80-93% ee). The reported hydrosilylation occurs at ambient temperatures (40 °C), with excellent functional group tolerability. Even ketones bearing heterocyclic substituents (e.g., pyridine or thiophene) or complex organic architectures are hydrosilylated efficiently, which is discussed further in this report.
Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand
Garbe, Marcel,Wei, Zhihong,Tannert, Bianca,Spannenberg, Anke,Jiao, Haijun,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias
supporting information, p. 1913 - 1920 (2019/03/13)
The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. (Figure presented.).