Reversible aryl migrations in metallated ureas: controlled inversion of configuration at a quaternary carbon atom

被引：13

作者：

Tetlow, Daniel J. ^{[1
]}

Vincent, Mark A. ^{[1
]}

Hillier, Ian H. ^{[1
]}

Clayden, Jonathan ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

ALPHA-ARYLATION; AMINES;

D O I：

10.1039/c2cc38704b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Deprotonation with strong bases of N-vinyl ureas carrying an N'-aryl substituent leads to migration of the N'-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents alpha to the urea N atom may migrate from C to N.

引用

页码：1548 / 1550

页数：3

共 21 条

[1] α-Arylation of Cyclic Amines by Aryl Transfer in Lithiated Ureas [J].

Bach, Renaud ;

Clayden, Jonathan ;

Hennecke, Ulrich .

SYNLETT, 2009, (03) :421-424

[2] α-pyridylation of chiral amines via urea coupling, lithiation and rearrangement [J].

Clayden, Jonathan ;

Hennecke, Ulrich .

ORGANIC LETTERS, 2008, 10 (16) :3567-3570

[3] Substituted diarylmethylamines by stereospecific intramolecular electrophilic arylation of lithiated ureas [J].

Clayden, Jonathan ;

Dufour, Jeremy ;

Grainger, Damian M. ;

Helliwell, Madeleine .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (24) :7488-+

[4] Tandem β-Alkylation-α-Arylation of Amines by Carbolithiation and Rearrangement of N-Carbamoyl Enamines (Vinyl Ureas) [J].

Clayden, Jonathan ;

Donnard, Morgan ;

Lefranc, Julien ;

Minassi, Alberto ;

Tetlow, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (19) :6624-+

[5] Peptide Coupling Reagents, More than a Letter Soup [J].

El-Faham, Ayman ;

Albericio, Fernando .

CHEMICAL REVIEWS, 2011, 111 (11) :6557-6602

[6] Rate-Determining Factors in Nucleophilic Aromatic Substitution Reactions [J].

Fernandez, Israel ;

Frenking, Gernot ;

Uggerud, Einar .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2971-2980

[7] Dyotropic Reactions: Mechanisms and Synthetic Applications [J].

Fernandez, Israel ;

Cossio, Fernando P. ;

Sierra, Miguel A. .

CHEMICAL REVIEWS, 2009, 109 (12) :6687-6711

[8] Lithium Choreography: Intramolecular Arylations of Carbamate-Stabilised Carbanions and Their Mechanisms Probed by In Situ IR Spectroscopy and DFT Calculations [J].

Fournier, Anne M. ;

Nichols, Christopher J. ;

Vincent, Mark A. ;

Hillier, Ian H. ;

Clayden, Jonathan .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (51) :16478-16490

[9]

Frisch M. J., 2016, Gaussian 03 Revision B.03

[10] CARBON-CARBON BOND-CLEAVAGE BY THE HALLER-BAUER AND RELATED REACTIONS - A REVIEW [J].

GILDAY, JP ;

PAQUETTE, LA .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1990, 22 (02) :167-&

← 1 2 3 →