Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides

被引：20
作者：
Cabre, Albert [1 ,2 ]
Romagnoli, Elia [1 ]
Martinez-Balart, Pol [1 ]
Verdaguer, Xavier [1 ,2 ]
Riera, Antoni [1 ,2 ]
机构：
[1] BIST, Inst Res Biomed IRB Barcelona, Baldiri Reixac 10, Barcelona 08028, Spain
[2] Univ Barcelona, Fac Quim, Seccio Organ, Dept Quim Inorgan & Organ, Marti & Franques 1, E-08028 Barcelona, Spain
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 23期
关键词：
ASYMMETRIC HYDROGENATION; INDOLINES; LIGANDS; TARGETS; OLEFINS;
D O I：
10.1021/acs.orglett.9b03865
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched beta-aryl-beta-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.
引用
收藏
页码：9709 / 9713
页数：5
相关论文
共 62 条
  • [1] [Anonymous], RCS
  • [2] [Anonymous], ORG PROCESS RES DEV
  • [3] Extending the Substrate Scope in the Hydrogenation of Unfunctionalized Tetrasubstituted Olefins with Ir-P Stereogenic Aminophosphine-Oxazoline Catalysts
    Biosca, Maria
    Salomo, Ernest
    de la Cruz-Sanchez, Pol
    Riera, Antoni
    Verdaguer, Xavier
    Pamies, Oscar
    Dieguez, Montserrat
    [J]. ORGANIC LETTERS, 2019, 21 (03) : 807 - 811
  • [4] Blaser H.U., 2004, ASYMMETRIC CATALYSIS
  • [5] CC-1065 and the duocarmycins: Synthetic studies
    Boger, DL
    Boyce, CW
    Garbaccio, RM
    Goldberg, JA
    [J]. CHEMICAL REVIEWS, 1997, 97 (03) : 787 - 828
  • [6] Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines
    Cabre, Albert
    Verdaguer, Xavier
    Riera, Antoni
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) : 4196 - 4200
  • [7] Total Synthesis of (R)-Sarkomycin Methyl Ester via Regioselective Intermolecular Pauson-Khand Reaction and Iridium-Catalyzed Asymmetric Isomerization
    Cabre, Albert
    Khaizourane, Helea
    Garcon, Marti
    Verdaguer, Xavier
    Riera, Antoni
    [J]. ORGANIC LETTERS, 2018, 20 (13) : 3953 - 3957
  • [8] Discovery and Optimization of Pyrimidone Indoline Amide P13Kβ Inhibitors for the Treatment of Phosphatase and Tensin Homologue (PTEN)-Deficient Cancers
    Certal, Victor
    Carry, Jean-Christophe
    Halley, Frank
    Virone-Oddos, Angela
    Thompson, Fabienne
    Filoche-Romme, Bruno
    El-Ahmad, Youssef
    Karlsson, Andreas
    Charrier, Veronique
    Delorme, Cecile
    Rak, Alexey
    Abecassis, Pierre-Yves
    Amara, Celine
    Vincent, Loic
    Bonnevaux, Helene
    Nicolas, Jean-Paul
    Mathieu, Magali
    Bertrand, Thomas
    Marquette, Jean-Pierre
    Michot, Nadine
    Benard, Tsiala
    Perrin, Marc-Antoine
    Lemaitre, Olivier
    Guerif, Stephane
    Perron, Sebastien
    Monget, Sylvie
    Gruss-Leleu, Florence
    Doerflinger, Gilles
    Guizani, Houlfa
    Brollo, Maurice
    Delbarre, Laurence
    Benin, Luc
    Richepin, Patrick
    Loyau, Veronique
    Garcia-Echeverria, Carlos
    Lengauer, Christoph
    Schio, Laurent
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (03) : 903 - 920
  • [9] Cornils B., 2002, Applied homogeneous catalysis with organometallic compounds
  • [10] Enantioselective synthesis of β-amino esters and its application to the synthesis of the enantiomers of the antidepressant Venlafaxine
    Davies, Huw M. L.
    Ni, Aiwu
    [J]. CHEMICAL COMMUNICATIONS, 2006, (29) : 3110 - 3112
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