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
来源：
ORGANIC LETTERS | 2000年 / 2卷 / 07期
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
  • [1] Synthesis of chiral 1,2-diamines by asymmetric lithiation-substitution
    Coldham, I
    Copley, RCB
    Haxell, TFN
    Howard, S
    ORGANIC LETTERS, 2001, 3 (23) : 3799 - 3801
  • [2] Asymmetric lithiation-substitution sequences of substituted allylamines
    Kim, DD
    Lee, SJ
    Beak, P
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14): : 5376 - 5386
  • [3] Asymmetric lithiation-substitution of amines involving rearrangement of borates
    Coldham, Iain
    Patel, Jignesh J.
    Raimbault, Sophie
    Whittaker, David T. E.
    Adams, Harry
    Fang, Guang Y.
    Aggarwal, Varinder K.
    ORGANIC LETTERS, 2008, 10 (01) : 141 - 143
  • [4] Synthesis of sparteine-like chiral diamines and evaluation in the enantioselective lithiation-substitution of N-(tert-butoxycarbonyl)pyrrolidine
    Hermet, JPR
    Porter, DW
    Dearden, MJ
    Harrison, JR
    Koplin, T
    O'Brien, P
    Parmene, J
    Tyurin, V
    Whitwood, AC
    Gilday, J
    Smith, NM
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (22) : 3977 - 3988
  • [5] Novel chiral aminophosphine ligand: Synthesis and application in asymmetric catalytic hydrogenation reaction
    Chen, YX
    Li, YM
    Lam, KH
    Chan, ASC
    CHINESE JOURNAL OF CHEMISTRY, 2003, 21 (01) : 66 - 70
  • [6] Novel Chiral Aminophosphine Ligand: Synthesis and Application in Asymmetric Catalytic Hydrogenation Reaction
    陈亿新
    李月明
    林剑虹
    陈新滋
    ChineseJournalofChemistry, 2003, (01) : 66 - 70
  • [7] Is the A-ring of sparteine essential for high enantioselectivity in the asymmetric lithiation-substitution of N-Boc-pyrrolidine?
    Phuan, PW
    Ianni, JC
    Kozlowski, MC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) : 15473 - 15479
  • [8] Synthesis of a water-soluble cationic chiral diamine ligand bearing a diguanidinium and application in asymmetric transfer hydrogenation
    Tang, Yuanfu
    Li, Xuefeng
    Lian, Chunxia
    Zhu, Jin
    Deng, Jingen
    TETRAHEDRON-ASYMMETRY, 2011, 22 (14-15) : 1530 - 1535
  • [9] Synthesis of a novel cubane-based chiral ligand and its application in asymmetric reactions
    Ingalsbe, Michelle L.
    Priefer, Ronny
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [10] Synthesis of novel chiral diallylic diamine
    Wang, H
    Pei, WW
    Wang, Y
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (12) : 1615 - 1618
12345