Lithium Enolates Derived from Pyroglutaminol: Mechanism and Stereoselectivity of an Azaaldol Addition

Michael J. Houghton; Christopher J. Huck; Stephen W. Wright; David B. Collum

doi:10.1021/jacs.6b05481

Lithium Enolates Derived from Pyroglutaminol: Mechanism and Stereoselectivity of an Azaaldol Addition

Journal of the American Chemical Society ◽

10.1021/jacs.6b05481 ◽

2016 ◽

Vol 138 (32) ◽

pp. 10276-10283 ◽

Cited By ~ 7

Author(s):

Michael J. Houghton ◽

Christopher J. Huck ◽

Stephen W. Wright ◽

David B. Collum

Keyword(s):

Lithium Enolates

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Additions and Corrections - Transition-State Modeling in Acyclic Stereoselection. A Molecular Mechanics Model for the Kinetic Formation of Lithium Enolates

Journal of the American Chemical Society ◽

10.1021/ja00302a600 ◽

1985 ◽

Vol 107 (16) ◽

pp. 4804-4804

Author(s):

David Moreland ◽

William Dauben

Keyword(s):

Transition State ◽

Molecular Mechanics ◽

Mechanics Model ◽

Lithium Enolates ◽

Molecular Mechanics Model

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ChemInform Abstract: Studies on N-Metalloimines: Synthesis of N-Unsubstituted Aziridines ( VI), (VII) from N-Trimethylsilylimines (III), and Lithium Enolates (V) of α-Halo Esters.

ChemInform ◽

10.1002/chin.199149144 ◽

2010 ◽

Vol 22 (49) ◽

pp. no-no

Author(s):

G. CAINELLI ◽

M. PANUNZIO ◽

D. GIACOMINI

Keyword(s):

Lithium Enolates

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The chemistry of metallacyclic alkenylcarbene complexes, 3. CC bond formation with carbon nucleophiles. stereoselective dienylation of lithium enolates and cuprates and a novel cascade synthesis of highly substituted cyclopentenones from lithium acetylides

Chemische Berichte ◽

10.1002/cber.19961290411 ◽

1996 ◽

Vol 129 (4) ◽

pp. 427-433 ◽

Cited By ~ 11

Author(s):

Jutta Böhmer ◽

Walter Förtsch ◽

Frank Hampel ◽

Rainer Schobert

Keyword(s):

Bond Formation ◽

Carbon Nucleophiles ◽

Lithium Enolates

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Solvent-Controlled Diastereoselective Synthesis of Cyclopentane Derivatives by a [3 + 2] Cyclization Reaction of α,β-Disubstituted (Alkenyl)(methoxy)carbene Complexes with Methyl Ketone Lithium Enolates

Journal of the American Chemical Society ◽

10.1021/ja029170x ◽

2003 ◽

Vol 125 (9) ◽

pp. 2610-2616 ◽

Cited By ~ 25

Author(s):

José Barluenga ◽

Jorge Alonso ◽

Francisco J. Fañanás

Keyword(s):

Methyl Ketone ◽

Cyclization Reaction ◽

Diastereoselective Synthesis ◽

Carbene Complexes ◽

Lithium Enolates

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Studies on N-metallo imines: synthesis of N-unsubstituted aziridines from N-trimethylsilyl imine and lithium enolates of α-halo esters.

Tetrahedron Letters ◽

10.1016/s0040-4039(00)71234-2 ◽

1991 ◽

Vol 32 (1) ◽

pp. 121-124 ◽

Cited By ~ 39

Author(s):

Gianfranco Cainelli ◽

Mauro Panunzio ◽

Daria Giacomini

Keyword(s):

Lithium Enolates

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ChemInform Abstract: Michael Addition Reactions of Unsaturated Esters with Lithium Enolates Derived from Vinylogous Urethanes.

ChemInform ◽

10.1002/chin.198726164 ◽

1987 ◽

Vol 18 (26) ◽

Author(s):

R. SCHLESSINGER ◽

P. LIN ◽

M. POSS ◽

J. SPRINGER

Keyword(s):

Michael Addition ◽

Addition Reactions ◽

Unsaturated Esters ◽

Lithium Enolates

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Umpolung of Fluoroform by CF Bond Activation: Direct Difluoromethylation of Lithium Enolates

Angewandte Chemie ◽

10.1002/ange.201203588 ◽

2012 ◽

Vol 124 (38) ◽

pp. 9673-9676 ◽

Cited By ~ 36

Author(s):

Toshiaki Iida ◽

Ryota Hashimoto ◽

Kohsuke Aikawa ◽

Shigekazu Ito ◽

Koichi Mikami

Keyword(s):

Bond Activation ◽

Lithium Enolates

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.alpha.-Halocarbonyl compounds. II. Position-specific preparation of .alpha.-bromoketones by bromination of lithium enolates. Position-specific introduction of .alpha.,.beta.-unsaturation into unsymmetrical ketones

The Journal of Organic Chemistry ◽

10.1021/jo00954a045 ◽

1973 ◽

Vol 38 (14) ◽

pp. 2576-2578 ◽

Cited By ~ 68

Author(s):

Phillip L. Stotter ◽

Kenneth A. Hill

Keyword(s):

Lithium Enolates ◽

Alpha Beta ◽

Halocarbonyl Compounds

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Synthesis of 2-[1-(Alkoxycarbonyl)alkyl]-3-methylbenzothiazolines and 3-Methyl-2-(2-oxoalkyl)benzothiazolines by the Direct Alkylation of Lithium Enolates with 3-Methylbenzothiazolium Salts

Bulletin of the Chemical Society of Japan ◽

10.1246/bcsj.62.3389 ◽

1989 ◽

Vol 62 (10) ◽

pp. 3389-3391 ◽

Cited By ~ 7

Author(s):

Hidenori Chikashita ◽

Naoto Takegami ◽

Yoshiyuki Yanase ◽

Kazuyoshi Itoh

Keyword(s):

Lithium Enolates

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The facile dearomatization of nitroaromatic compounds using lithium enolates of unsaturated ketones in conjugate additions and (4+2) formal cycloadditions

Chemical Communications ◽

10.1039/c9cc02924a ◽

2019 ◽

Vol 55 (52) ◽

pp. 7494-7497 ◽

Cited By ~ 5

Author(s):

Karine Pasturaud ◽

Batoul Rkein ◽

Morgane Sanselme ◽

Muriel Sebban ◽

Sami Lakhdar ◽

...

Keyword(s):

Nitroaromatic Compounds ◽

The Novel ◽

Conjugate Additions ◽

Unsaturated Ketones ◽

Lithium Enolates

The novel nucleophilic activation of enolizable unsaturated ketones allows their addition to nitroaromatics and furnishes the corresponding formal dearomatized (4+2) cycloadducts.

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