Chiral bidentate lithium amides having a chiral amide nitrogen for enantioselective deprotonation of 4-tert-butylcycloxexanone

被引：0
|
作者：
Chatani, H [1 ]
Nakajima, M [1 ]
Kawasaki, K [1 ]
Koga, K [1 ]
机构：
[1] Univ Tokyo, Fac Pharmaceut Sci, Bunkyo Ku, Tokyo 113, Japan
来源：
HETEROCYCLES | 1997年 / 46卷
关键词：
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective deprotonation of 4-tert-butylcyclohexanone (1) by chiral bidentate lithium amides ((R)-5a similar to b) was examined in the presence of excess TMSCl in several solvents containing 2 equivalents of HMPA. The sense of asymmetric induction was found to be the same with that by using (R)-2a similar to b. This result suggests the formation of a similar chiral amide nitrogen in these chiral lithium amides.
引用
收藏
页码：53 / 56
页数：4
相关论文
共 50 条
  • [41] Enantioselective synthesis of phospholanes using chiral lithium amide desymmetrisation
    Blake, AJ
    Hume, SC
    Li, WS
    Simpkins, NS
    TETRAHEDRON, 2002, 58 (23) : 4589 - 4602
  • [42] CHIRAL LITHIUM AMIDES - BETA-ELIMINATION OF TRITYLLITHIUM FROM A LITHIUM AMIDE
    PLAQUEVENT, JC
    RAVARD, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 361 (03) : C51 - C53
  • [43] Solid-phase supported chiral lithium amides used in deprotonation reactions
    Johansson, A
    Abrahamsson, P
    Davidsson, Ö
    TETRAHEDRON-ASYMMETRY, 2003, 14 (10) : 1261 - 1266
  • [44] Enantioselective conjugate addition of a lithium ester enolate catalyzed by chiral lithium amides
    Duguet, Nicolas
    Harrison-Marchand, Anne
    Maddaluno, Jacques
    Tomioka, Kiyoshi
    ORGANIC LETTERS, 2006, 8 (25) : 5745 - 5748
  • [45] New Potentially Chelating Chiral Magnesium Amide Bases for Use in Enantioselective Deprotonation Reactions
    Kerr, William J.
    Middleditch, Michael
    Watson, Allan J. B.
    SYNLETT, 2011, (02) : 177 - 180
  • [46] Enantioselective deprotonation reactions using polymer-supported chiral magnesium amide basest
    Henderson, KW
    Kerr, WJ
    Moir, JH
    CHEMICAL COMMUNICATIONS, 2001, (18) : 1722 - 1723
  • [47] Computational study of solvation and stereoselectivity in deprotonation of cyclohexene oxide by a chiral lithium amide
    Lill, SON
    Arvidsson, PI
    Ahlberg, P
    TETRAHEDRON-ASYMMETRY, 1999, 10 (02) : 265 - 279
  • [48] Composition of the activated complex in the stereoselective deprotonation of cyclohexene oxide by a chiral lithium amide
    Olsson, RI
    Ahlberg, P
    TETRAHEDRON-ASYMMETRY, 1999, 10 (20) : 3991 - 3998
  • [49] Enantioselective Annulation Reactions Enabled by Chiral Lithium Amides as Traceless Auxiliaries
    Lu, Leroy
    Sepetov, Lev N.
    Purcell, Lauren
    Park, Jessica
    Pan, Priscilla Y.
    Yu, Kai
    Zakarian, Armen
    ORGANIC LETTERS, 2025, 27 (06) : 1487 - 1491
  • [50] Stereoselective reactions .26. Solution structures of a chiral bidentate lithium amide in relation to the solvent-dependent enantioselectivities in deprotonation reaction
    Sato, D
    Kawasaki, H
    Shimada, I
    Arata, Y
    Okamura, K
    Date, T
    Koga, K
    TETRAHEDRON, 1997, 53 (21) : 7191 - 7200
12345