Enantiomerization Dynamics and a Catalytic Dynamic Resolution of N-Trimethylallyl-2-lithiopyrrolidine

被引:16
作者
Beng, Timothy K. [1 ]
Yousaf, Taher I. [1 ]
Coldham, Iain [2 ]
Gawley, Robert E. [1 ]
机构
[1] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA
[2] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
基金
美国国家科学基金会;
关键词
HIGHLY ENANTIOSELECTIVE REACTIONS; ALPHA-SULFONYL CARBANIONS; THERMODYNAMIC RESOLUTION; KINETIC RESOLUTION; NMR-SPECTROSCOPY; 2-LITHIOPYRROLIDINES; N-BOC-2-LITHIOPYRROLIDINE; EQUILIBRATION; BARRIER;
D O I
10.1021/ja900755a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The barriers to enantiomerization of N-trimethylallyl-2-lithiopyrrolidine have been measured in the presence of sparteine, 1, N,N'-diisopropylbispidine, 2, and diaminoalkoxide 3. We have additionally demonstrated a rare example of a catalytic dynamic resolution using either of two ligands, achieving enantiomer ratios of up to 93:7.
引用
收藏
页码:6908 / +
页数:3
相关论文
共 18 条
  • [1] Barrier to enantiomerization of unstabilized, chelated, and dipole-stabilized 2-lithiopyrrolidines
    Ashweek, NJ
    Brandt, P
    Coldham, I
    Dufour, S
    Gawley, RE
    Hæffner, F
    Klein, R
    Sanchez-Jimenez, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) : 449 - 457
  • [2] Dynamic thermodynamic resolution: Control of enantioselectivity through diastereomeric equilibration
    Beak, P
    Anderson, DR
    Curtis, MD
    Laumer, JM
    Pippel, DJ
    Weisenburger, GA
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (10) : 715 - 727
  • [3] Beak P, 2003, TOP ORGANOMETAL CHEM, V5, P139
  • [4] Clayden J., 2002, ORGANOLITHIUMS SELEC
  • [5] Dynamic kinetic resolution of N-Boc-2-lithiopyrrolidine
    Coldham, I
    Patel, JJ
    Sanchez-Jimenez, G
    [J]. CHEMICAL COMMUNICATIONS, 2005, (24) : 3083 - 3085
  • [6] Dynamic thermodynamic and dynamic kinetic resolution of 2-lithiopyrrolidines
    Coldham, Iain
    Dufour, Samuel
    Haxell, Thomas F. N.
    Patel, Jignesh J.
    Sanchez-Jimenez, Graciela
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) : 10943 - 10951
  • [7] Structural studies of {6Li} 2-lithiopyrrolidines using NMR spectroscopy
    Gawley, RE
    Klein, R
    Ashweek, NJ
    Coldham, I
    [J]. TETRAHEDRON, 2005, 61 (13) : 3271 - 3280
  • [8] Hodgson D.M., 2003, ORGANOLITHIUMS ENANT
  • [9] Hoppe D, 1997, ANGEW CHEM INT EDIT, V36, P2283
  • [10] Dynamic Thermodynamic Resolution: Advantage by Separation of Equilibration and Resolution
    Lee, Won Koo
    Park, Yong Sun
    Beak, Peter
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) : 224 - 234