Synthesis and resolution of a novel chiral diamine ligand and application to asymmetric lithiation-substitution

被引:62
|
作者
Li, XL [1 ]
Schenkel, LB [1 ]
Kozlowski, MC [1 ]
机构
[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol9903133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A short, efficient synthesis of chiral 1,5-diaza-cis-decalins (7) is presented. In the lithiation of N-Boc pyrrolidine, the ligands with the smallest most electron rich R groups (Me > Et > (CH2Bu)-Bu-t > CH2CF3 approximate to Bn) were most effective. In the asymmetric deprotonation/substitution of benzylic substrates, (R,R)-7 (R = Me, R' = H) conferred modest selectivity. The ready availability of both enantiomers of the 1,5-diaza-cis-decalins and the ability to tune steric and electronic properties renders these compounds an attractive new class of diamine ligands.
引用
收藏
页码:875 / 878
页数:4
相关论文
共 50 条
  • [41] Synthesis of polymer-supported chiral 1,2-diamine by polycondensation and its application to asymmetric hydrogenation
    Haraguchi, Naoki
    Prasad, Nilesh Anand
    Uchiyama, Takao
    Itsuno, Shinichi
    WMSCI 2006: 10TH WORLD MULTI-CONFERENCE ON SYSTEMICS, CYBERNETICS AND INFORMATICS, VOL III, PROCEEDINGS, 2006, : 3 - 4
  • [42] Synthesis of polymer-supported chiral 1,2-diamine and its application to asymmetric hydrogenation of acetophenone
    Itsuno, S
    Tsuji, A
    Takahashi, M
    DESIGNED MONOMERS AND POLYMERS, 2004, 7 (06) : 495 - 503
  • [43] Synthesis of chiral 1,2-diamine immobilized on polystyrene and its application to asymmetric hydrogenation of aromatic ketones
    Takahashi, M
    Tsuji, A
    Chiba, M
    Itsuno, S
    REACTIVE & FUNCTIONAL POLYMERS, 2005, 65 (1-2): : 1 - 8
  • [44] Synthesis and resolution of chiral N,N-diaryl diamine compounds
    Harpainter, Phoebe
    Roland, Sylvain
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 241
  • [45] SYNTHESIS OF THE NOVEL CHIRAL POLYMERS WITH MULTIDENTATE LIGAND AND RESOLUTION OF DL-AMINO ACIDS
    金仁华
    何炳林
    Science in China,SerB., 1989, Ser.B.1989 (06) : 650 - 660
  • [46] SYNTHESIS OF THE NOVEL CHIRAL POLYMERS WITH MULTIDENTATE LIGAND AND RESOLUTION OF DL-AMINO ACIDS
    JIN, RH
    HE, BL
    SCIENCE IN CHINA SERIES B-CHEMISTRY, 1989, 32 (06): : 650 - 660
  • [47] Synthesis and Characterization of Aromatic Diamine and Its Polyimides with Asymmetric Structure and Trifluoromethyl Substitution
    Yu B.
    Zhou Y.
    Gao P.
    Wang C.
    Zhao X.
    Li J.
    Ren Q.
    Gaofenzi Cailiao Kexue Yu Gongcheng/Polymeric Materials Science and Engineering, 2019, 35 (09): : 14 - 20
  • [48] A novel chiral base mediated glutarimide desymmetrisation: Application to the asymmetric synthesis of (-)-paroxetine
    Greenhalgh, DA
    Simpkins, NS
    SYNLETT, 2002, (12) : 2074 - 2076
  • [49] APPLICATION OF CHIRAL LIGAND POLYMERS IN RESOLUTION OF OPTICAL ISOMERS
    何炳林
    Progress in Natural Science Communication of State Key Laboratories of China, 1991, (06) : 505 - 514
  • [50] New chiral phosphinoimidazolidine ligand in palladium-catalyzed asymmetric allylic substitution
    Jin, MJ
    Kim, SH
    Lee, SJ
    Kim, YM
    TETRAHEDRON LETTERS, 2002, 43 (41) : 7409 - 7411