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Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of alpha-Alkyl-beta-ketoesters via Dynamic Kinetic Resolution
Hou, Chuan-Jin1,2; Hu, Xiang-Ping1
Source PublicationORGANIC LETTERS
2016-11-04
DOI10.1021/acs.orglett.6b02828
Volume18Issue:21Pages:5592-5595
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Organic
WOS KeywordKETO ESTER HYDROCHLORIDES ; FORMAL 3+2 CYCLOADDITION ; DECARBOXYLATIVE PROPARGYLIC ALKYLATION ; 3-OXO CARBOXYLIC ESTERS ; AMINO ACID-ESTERS ; ASYMMETRIC HYDROGENATION ; ENANTIOSELECTIVE HYDROGENATION ; IRIDIUM CATALYSTS ; STEREOSELECTIVE-SYNTHESIS ; DIPHOSPHINE LIGANDS
AbstractA new class of sterically hindered chiral ferrocenyl P,N,N-ligands have been prepared through a two-step transformation from (S-c,R-p)-PPFNH2, in which a new (R)-stereogenic center at the pyridinylmethyl position was generated in high diastereoselectivity. With these newly developed P,N,N-ligands, Ir-catalyzed asymmetric hydrogenation of various alpha-alkyl substituted beta-aryl-beta-ketoesters via dynamic kinetic resolution has been realized in high diastereo- and enantioselectivities for the first time, which led to a variety of optically active anti-beta-hydroxyesters in up to 99% ee. The study indicated that the additional stereocenter at the pyridinylmethyl position of these ligands is crucial to realize this hydrogenation.
Language英语
WOS IDWOS:000387303200037
Citation statistics
Cited Times:10[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/150350
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China
2.Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Peoples R China
Recommended Citation
GB/T 7714
Hou, Chuan-Jin,Hu, Xiang-Ping. Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of alpha-Alkyl-beta-ketoesters via Dynamic Kinetic Resolution[J]. ORGANIC LETTERS,2016,18(21):5592-5595.
APA Hou, Chuan-Jin,&Hu, Xiang-Ping.(2016).Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of alpha-Alkyl-beta-ketoesters via Dynamic Kinetic Resolution.ORGANIC LETTERS,18(21),5592-5595.
MLA Hou, Chuan-Jin,et al."Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of alpha-Alkyl-beta-ketoesters via Dynamic Kinetic Resolution".ORGANIC LETTERS 18.21(2016):5592-5595.
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