Functionalized α-oximinoketones as building blocks for the construction of imidazoline-based potential chiral auxiliaries

被引：12

作者：

Gutierrez, Rsuini U. ^{[1
]}

Rebollar, Araceli ^{[1
]}

Bautista, Rafael ^{[1
,2
]}

Pelayo, Vanessa ^{[1
]}

Luis Vargas, Jose ^{[1
]}

Montenegro, Mabel M. ^{[1
]}

Espinoza-Hicks, Carlos ^{[1
]}

Ayala, Francisco ^{[1
]}

Bernal, Pablo M. ^{[2
]}

Carrasco, Cuauhtemoc ^{[2
]}

Zepeda, L. Gerardo ^{[1
]}

Delgado, Francisco ^{[1
]}

Tamariz, Joaquin ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Mexico City 11340, DF, Mexico

[2] Signa SA CV, Dept Invest & Desarrollo, Toluca 50200, Edo De Mexico, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 04期

关键词：

COMBRETASTATIN A-4 ANALOGS; VITRO ANTITUMOR-ACTIVITY; SOLID-PHASE SYNTHESIS; AZOLE N-OXIDES; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; RECEPTOR ANTAGONISTS; DERIVATIVES; ALDOL;

D O I：

10.1016/j.tetasy.2015.01.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Functionalized alpha-oximinoketones with beta-alkoxy, beta-alkyl, and beta-sulfenyl groups were used as efficient synthons for the preparation of chiral 1-acyl-4-imidazolin-2-ones and 1-acylimidazolidin-2-ones. For the preparation of the former heterocycles, alpha-oximinoketones were transformed into their respective imidazole N-oxides by neutral treatment with a chiral triazine, followed by reaction with acetic or propionic anhydrides to furnish the desired chiral 1-acetyl- or 1-propionyl-4-imidazolin-2-ones in moderate overall yields. Upon palladium hydroxide-catalyzed hydrogenation, these series were converted into their corresponding 1-acylimidazolidin-2-ones in high diastereoisomeric ratios. Thus, these novel chiral 1-acetyl- and 1-propionyl-imidazolidin-2-ones were obtained with a variety of alkyl groups at the C-4 and C-5 positions of the heterocycle, through a three-step methodology, and can be applied as new potential chiral auxiliaries. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：230 / 246

页数：17

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