Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol

被引：5

作者：

Brusentsev, Yury ^{[1
]}

Sandberg, Thomas ^{[2
]}

Hotokka, Matti ^{[2
]}

Sjoholm, Rainer ^{[1
]}

Eklund, Patrik ^{[1
]}

机构：

[1] Abo Akad Univ, Organ Chem Lab, SF-20500 Turku, Finland

[2] Abo Akad Univ, Phys Chem Lab, SF-20500 Turku, Finland

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 09期

基金：

芬兰科学院;

关键词：

Lignans; Hydroxymatairesinol; Chiral 1,4-diol; Asymmetric catalysis; Ab initio calculations; ENANTIOSELECTIVE ADDITION; TADDOL ANALOGS; DIETHYLZINC;

D O I：

10.1016/j.tetlet.2012.12.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The readily available natural lignan hydroxymatairesinol was transformed into sterically hindered and optically pure diphenyl, di-2-naphthyl, and tetramethyl 1,4-diol derivatives via mylation/alkylation of the aryltetralinbutyrolactone lignan (-)-conidendrin. In addition, the diastereoselective formation of stable hemiketals from the highly substituted butyrolactone was studied in detail. The conformations of the molecules prepared were studied computationally at molecular mechanics (MM), Hartree-Fock (HF)/6-31G*, and (DFT/B3LYP/TZVP) levels including entropy contributions and by NMR-spectroscopy. The conformations adopted showed that these novel chiral 1,4-diols may be suitable as chiral ligands for the development of new chiral transition metal and organo catalysts. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：1112 / 1115

页数：4

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