Electrogenerated N-heterocyclic carbene: N-acylation of chiral oxazolidin-2-ones in ionic liquids

被引：27

作者：

Chiarotto, Isabella ^{[1
]}

Feeney, Michelle M. M. ^{[1
]}

Feroci, Marta ^{[1
]}

Inesi, Achille ^{[1
]}

机构：

[1] Univ Roma La Sapienza, Dipartimento Ingn Chim Mat Ambiente, I-00161 Rome, Italy

来源：

ELECTROCHIMICA ACTA | 2009年 / 54卷 / 05期

关键词：

Chiral auxiliaries; Ionic liquid; Electrochemistry; Oxazolidin-2-ones; Acylation; ASYMMETRIC-SYNTHESIS; CARBOXYLIC-ACIDS; ALDOL REACTIONS; BOND FORMATION; ELECTROCHEMISTRY; OXAZOLIDINONES; IMIDE;

D O I：

10.1016/j.electacta.2008.09.057

中图分类号：

O646 [电化学、电解、磁化学];

学科分类号：

081704 ;

摘要：

An electrochemical procedure for the N-acylation of chiral oxazolidin-2-ones, in the absence of volatile molecular organic solvents, has been set up via electrolyses of ionic liquid [bmim]BF(4) containing oxazolidin-2-ones followed by addition of saturated or unsaturated anhydrides. N-acyloxazolidin-2-ones were isolated in good to elevated yields. The electrochemically induced N-acylation of chiral oxazolidin-2-ones occurs with total retention of the absolute configuration of all the chiral atoms. The electrogenerated carbene (1-butyl-3-methyl-1H-imidazol-2-ylidene) has been indicated as the base involved in the deprotonation of chiral oxazolidin-2-ones. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1638 / 1644

页数：7

共 26 条

[1]

Ager DJ, 1997, ALDRICHIM ACTA, V30, P3

[2]

AGER DJ, 1996, CHEM REV, V96, P5

[3] Diastereoselective conjugate addition of cyanide to α,β-unsaturated oxazolidinones:: Enantioselective synthesis of ent-pregabalin and baclofen [J].

Armstrong, Alan ;

Convine, Nicola J. ;

Popkin, Matthew E. .

SYNLETT, 2006, (10) :1589-1591

[4] A critical assessment of electrochemistry in a distillable room temperature ionic liquid, DIMCARB [J].

Bhatt, AI ;

Bond, AM ;

MacFarlane, DR ;

Zhang, J ;

Scott, JL ;

Strauss, CR ;

Iotov, PI ;

Kalcheva, SV .

GREEN CHEMISTRY, 2006, 8 (02) :161-171

[5] Non-haloaluminate room-temperature ionic liquids in electrochemistry - A review [J].

Buzzeo, MC ;

Evans, RG ;

Compton, RG .

CHEMPHYSCHEM, 2004, 5 (08) :1106-1120

[6]

Crimmins MT, 2004, SYNLETT, P1371

[7]

Evans D.A., 1982, Aldrichimica Acta, V15, P23

[8] Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones [J].

Evans, DA ;

Tedrow, JS ;

Shaw, JT ;

Downey, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) :392-393

[9] Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes [J].

Evans, DA ;

Scheidt, KA ;

Johnston, JN ;

Willis, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4480-4491

[10] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

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