253327-94-5Relevant articles and documents
H8-MonoPhos and its application in catalytic enantioselective hydrogenation of α-dehydroamino acids
Zeng, Qingle,Liu, Hui,Mi, Aiqiao,Jiang, Yaozhong,Li, Xingshu,Choi, Michael C.K,Chan, Albert S.C
, p. 8799 - 8803 (2002)
H8-MonoPhos, a new stable and readily soluble monodentate phosphoramidite ligand, has been facilely prepared from H8-BINOL. The ligand achieved up to 99.9% ee and 96.7% ee in hydrogenation of dehydroalanine and dehydrohomophenylalani
Site-Selective Modification of α-Amino Acids and Oligopeptides via Native Amine-Directed γ-C(sp3)-H Arylation
Yuan, Feipeng,Hou, Zhen-Lin,Pramanick, Pranab K.,Yao, Bo
supporting information, p. 9381 - 9385 (2019/11/28)
Site-selective modification of chemically and biologically valuable α-amino acids and peptides is of great importance for biochemical study and pharmaceutical development. Few methods based on remote C(sp3)-H functionalization of aliphatic side-chains of peptides has been disclosed in recent years. In this report, we developed a novel approach for γ-C(sp3)-H and γ-/δ-C(sp2)-H arylation of α-amino acids with α-hydrogen by native amine-directed C-H functionalization and further realized the γ-C(sp3)-H arylation of N-terminally unprotected peptides.
Enantioselective synthesis of optically pure β-amino ketones and γ-aryl amines by Rh-catalyzed asymmetric hydrogenation
Geng, Huiling,Huang, Kexuan,Sun, Tian,Li, Wei,Zhang, Xiaowei,Zhou, Le,Wu, Wenjun,Zhang, Xumu
, p. 332 - 334 (2011/03/19)
A series of optically pure β-amino ketones have been synthesized in high enantioselectivities (ee > 99%) by Rh-DuanPhos-catalyzed asymmetric hydrogenation of readily prepared β-keto enamides. Further reduction of these β-amino ketones with hydrogen and Pd/C leads to the formation of a variety of protected enantiomerically pure γ-aryl amines (ee > 99%), which are key building blocks in many bioactive molecules.
Impact on hydrogenation catalytic cycle of the R groups Cyclic feature in "r-SMS-Phos"
Zupancic, Borut,Mohar, Barbara,Stephan, Michel
supporting information; experimental part, p. 3022 - 3025 (2010/08/19)
A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ees also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.
