Absolute configuration assignment of 3-oxindolylacetyl-4-phenyloxazolidinone derivatives

被引：9

作者：

Suarez-Castillo, Oscar R. ^{[1
]}

Melendez-Rodriguez, Myriam ^{[1
]}

Castelan-Duarte, Luis E. ^{[1
]}

Zuniga-Estrada, Erick A. ^{[1
]}

Cruz-Borbolla, Julian ^{[1
]}

Morales-Rios, Martha S. ^{[2
]}

Joseph-Nathan, Pedro ^{[2
]}

机构：

[1] Univ Autonoma Estado Hidalgo, Area Acad Quim, Mineral De La Reforma 42184, Hidalgo, Mexico

[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 24期

关键词：

MOLECULAR-FORCE FIELD; 1ST TOTAL-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CLAISEN REARRANGEMENT; CALABAR ALKALOIDS; INDOLE ALKALOIDS; RICE BRAN; MMFF94; ACID; GEOMETRIES;

D O I：

10.1016/j.tetasy.2011.11.018

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The straightforward determination of the absolute configuration of 2-oxo-3-indolylacetic acid derivatives 5a-e, based on analysis of the H-1 NMR spectra of their oxindolylacetyl-phenyloxazolidinones 6a-e, is described. The conformational preferences for two diastereomeric amides were calculated by DFT, which matched well with the experimental results, while X-ray diffraction analysis allowed us to validate the methodology. Independent absolute configuration evidence was also obtained by vibrational circular dichroism. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2085 / 2098

页数：14

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