Metal-Free Synthesis of Indanes by Iodine(III)-Mediated Ring Contraction of 1,2-Dihydronaphthalenes

被引：26

作者：

Siqueira, Fernanda A. ^{[1
]}

Ishikawa, Eloisa E. ^{[1
]}

Fogaca, Andre ^{[1
]}

Faccio, Andrea T. ^{[1
]}

Carneiro, Vania M. T. ^{[1
]}

Soares, Rafael R. S. ^{[1
]}

Utaka, Aline ^{[1
]}

Tebeka, Iris R. M. ^{[1
]}

Bielawski, Marcin ^{[1
,2
]}

Olofsson, Berit ^{[2
]}

Silva, Luiz F., Jr. ^{[1
]}

机构：

[1] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, BR-05513970 Sao Paulo, Brazil

[2] Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2011年 / 22卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

indanes; hypervalent iodine; ring contraction; 1,2-dihydronaphthalenes; rearrangements; DIASTEREOSELECTIVE TOTAL-SYNTHESIS; HYPERVALENT IODINE REAGENTS; RECEPTOR ANTAGONISTS; POLYVALENT IODINE; ORGANIC-SYNTHESIS; OXIDATIVE REARRANGEMENTS; ELECTROPHILIC ADDITIONS; AROMATIC-COMPOUNDS; TETRACYCLIC CORE; KOSERS REAGENT;

D O I：

10.1590/S0103-50532011000900024

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A metal-free protocol was developed to synthesize indanes by ring contraction of 1,2-dihydronaphthalenes promoted by PhI(OH) OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2,2,2-trifluoroethanol (TFE), 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), and a 1: 4 mixture of TFE: CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1,3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry.

引用

页码：1795 / 1807

页数：13

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