Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides: A Possible Intermediate Characterized

被引：28
|
作者：
Lecachey, Baptiste [1 ,2 ]
Duguet, Nicolas [1 ,2 ]
Oulyadi, Hassan [1 ,2 ]
Fressigne, Catherine [1 ,2 ]
Harrison-Marchand, Anne [1 ,2 ]
Yamamoto, Yasutomo [3 ]
Tomioka, Kiyoshi [3 ]
Maddaluno, Jacques [1 ,2 ]
机构：
[1] Univ Rouen, IRCOF, CNRS, UMR 6014, F-76821 Mont St Aignan, France
[2] Univ Rouen, FR 3038, F-76821 Mont St Aignan, France
[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 09期
关键词：
DIISOPROPYLAMIDE-MEDIATED ENOLIZATIONS; MIXED AGGREGATION; N-BUTYLLITHIUM; NMR; COMPLEXES; SPECTROSCOPY; HALIDES;
D O I：
10.1021/ol900275y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two 1:1 noncovalent mixed aggregates between a lithium enolate and two diastereomeric lithium amides have been identified spectroscopically in THE The NMR data, as well as DFT theoretical calculations, shine some light on a puzzling reversal of induction, observed when switching from one diastereomer of the amide to the other in the enantioselective Michael addition of the lithium enolate to an unsaturated ester.
引用
收藏
页码：1907 / 1910
页数：4
相关论文
共 50 条
  • [41] NMR studies of a ternary complex reagent of lithium ester enolate, chiral diether, and lithium diisopropylamide in an asymmetric Michael reaction
    Yamamoto, Yasutomo
    Yasuda, Yorinobu
    Oulyadi, Hassan
    Maddaluno, Jacques
    Tomioka, Kiyoshi
    TETRAHEDRON, 2010, 66 (13) : 2470 - 2473
  • [42] The chiral ligand-catalyzed enantioselective conjugate addition of organolithium to BHA enoate
    Asano, Y
    Iida, A
    Tomioka, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1998, 46 (01) : 184 - 186
  • [43] Highly enantioselective conjugate addition of aldehydes to nitroolefins catalyzed by chiral bifunctional sulfamides
    Zhang, Xue-jing
    Liu, Sheng-ping
    Li, Xue-ming
    Yan, Ming
    Chan, Albert S. C.
    CHEMICAL COMMUNICATIONS, 2009, (07) : 833 - 835
  • [44] Chiral dihydroxytetraphenylene-catalyzed enantioselective conjugate addition of boronic acids to β-enaminones
    Yao, En-Ze
    Chai, Guo-Li
    Zhang, Ping
    Zhu, Bo
    Chang, Junbiao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09): : 2375 - 2381
  • [45] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS CATALYZED BY CHIRAL CUPRATE COMPLEXES
    AHN, KH
    LIPPARD, SJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 197 : 77 - ORGN
  • [46] Enantioselective copper-catalyzed conjugate addition using chiral diaminocarbene ligands
    Guillen, F
    Winn, CL
    Alexakis, A
    TETRAHEDRON-ASYMMETRY, 2001, 12 (15) : 2083 - 2086
  • [47] ENANTIOSELECTIVE ADDITION OF ALKYLLITHIUM REAGENTS TO ALDEHYDES INDUCED BY CHIRAL LITHIUM ALKOXIDES
    YE, MC
    LOGARAJ, S
    JACKMAN, LM
    HILLEGASS, K
    HIRSH, KA
    BOLLINGER, AM
    GROSZ, AL
    MANI, V
    TETRAHEDRON, 1994, 50 (20) : 6109 - 6116
  • [48] ENANTIOSELECTIVE ADDITION OF ALKYLLITHIUM REAGENTS TO ALDEHYDES INDUCED BY CHIRAL LITHIUM ALKOXIDES
    YE, MC
    LOGARAJ, S
    JACKMAN, LM
    HIRSH, KA
    GROSZ, A
    HILLEGASS, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 384 - ORGN
  • [49] ON THE WAY TO CHIRAL COPPER(I) ARENETHIOLATE CATALYSTS FOR THE ENANTIOSELECTIVE CONJUGATE ADDITION OF METHYL LITHIUM AND METHYL MAGNESIUM IODIDE TO BENZYLIDENEACETONE
    LAMBERT, F
    KNOTTER, DM
    JANSSEN, MD
    VANKLAVEREN, M
    BOERSMA, J
    VANKOTEN, G
    TETRAHEDRON-ASYMMETRY, 1991, 2 (11) : 1097 - 1100
  • [50] Enantioselective Cyanosilylation of Ketones with Lithium(I) Dicyanotrimethylsilicate(IV) Catalyzed by a Chiral Lithium(I) Phosphoryl Phenoxide
    Hatano, Manabu
    Yamakawa, Katsuya
    Kawai, Tomoaki
    Horibe, Takahiro
    Ishihara, Kazuaki
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (12) : 4021 - 4025
12345