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
收藏
页码：2085 / 2098
页数：14
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