SAMARIUM(II) IODIDE - A DIASTEREOSELECTIVE REAGENT FOR THE SYNTHESIS OF AROMATIC 1,2-DIOL STRUCTURES - MODEL REACTIONS

被引：7

作者：

WEGE, VU ^{[1
]}

GREINER, A ^{[1
]}

机构：

[1] ZENTRUM MAT WISSENSCH,D-35032 MARBURG,GERMANY

来源：

ACTA POLYMERICA | 1995年 / 46卷 / 05期

关键词：

D O I：

10.1002/actp.1995.010460508

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Variation of the reaction conditions for the C-C coupling reaction of aromatic carbonyl compounds to their 1,2-diol structures in the presence of samaraium(II)-iodide led to different diastereoselectivities. The molar ratio of the starting materials, substituents, and solvent variation had a significant influence on 1,2-diol formation. An interpretation of the observed results is suggested. Sterical demands of the active complex and an intramolecular samarium-oxygen interaction could lead to the diastereomer ratio obtained.

引用

收藏

页码：396 / 403

页数：8

相关论文

共 50 条

[31] A novel one-pot synthesis of cyclopentanol derivatives from aldehydes and α-haloketones by samarium (III) iodide and samarium (II) iodide mediated cascade reactions [J].

Fan, XS ;

Zhang, YM .

JOURNAL OF CHEMICAL RESEARCH-S, 2001, (03) :104-105

[32] Hydrogen Sulfide: A Reagent for pH-Driven Bioinspired 1,2-Diol Mono-deoxygenation and Carbonyl Reduction in Water [J].

Barata-Vallejo, Sebastian ;

Ferreri, Carla ;

Golding, Bernard T. ;

Chatgilialoglu, Chryssostomos .

ORGANIC LETTERS, 2018, 20 (14) :4290-4294

[33] The synthesis of amphipathic prodrugs of 1,2-diol drugs with saccharide conjugates by high regioselective enzymatic protocol [J].

Quan, Jing ;

Chen, Zhichun ;

Han, Chengyou ;

Lin, Xianfu .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (04) :1741-1748

[34] Asymmetric Amination of 1,2-Diol through Borrowing Hydrogen: Synthesis of Vicinal Amino α-Tertiary Alcohol [J].

Ali, Tariq ;

Rahman, Tahir ;

Perveen, Shahida ;

Wang, Lingyun ;

Khan, Ajmal .

CHEMISTRY-A EUROPEAN JOURNAL, 2025, 31 (21)

[35] Synthesis of Phenylacetaldehyde from 1-Phenylethan-1,2-diol by Microwave-Assisted Dehydration in Water [J].

Sarah Le Guenic ;

Claire Ceballos ;

Christophe Len .

Catalysis Letters, 2015, 145 :1851-1855

[36] Samarium(II) iodide promoted synthesis of 1-ethoxycarbonylmethyl-2-hydrofullerene [J].

Zhang, S ;

Gan, LB ;

Huang, CH ;

He, XR .

CHINESE CHEMICAL LETTERS, 2000, 11 (04) :289-292

[37] DIRECT SYNTHESIS OF MONOCARBAMIC ESTER OF 1,2-DIOL FROM CARBON-DIOXIDE, EPOXIDE AND AMINE [J].

YOSHIDA, Y ;

INOUE, S .

CHEMISTRY LETTERS, 1978, (02) :139-140

[38] STEREOSELECTIVE SYNTHESIS OF MAITOTOXIN GHI-RING SYSTEM HAVING A 1,2-DIOL SIDE CHAIN [J].

Nagatomo, Masanori ;

Nakata, Tadashi .

HETEROCYCLES, 2008, 76 (02) :1069-1074

[39] An efficient preparation of (R*,R*)-1,2-dicyclohexylethane-1,2-diol, a superior chiral director for synthesis with boronic esters [J].

Hiscox, WC ;

Matteson, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8315-8316

[40] REACTIONS OF CARBONYL-COMPOUNDS WITH BENZYL CHLOROMETHYL ETHER OF DIIODOMETHANE IN THE PRESENCE OF SAMARIUM(II) IODIDE OR METALLIC SAMARIUM - NEW ROUTES TO 1,2-DIOLS, IODOHYDRINS AND CYCLOPROPANOLS [J].

IMAMOTO, T ;

HATAJIMA, T ;

TAKIYAMA, N ;

TAKEYAMA, T ;

KAMIYA, Y ;

YOSHIZAWA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3127-3135

← 1 2 3 4 5 →