Oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III)

被引：34

作者：

Ahmad, Anees ^{[1
]}

Scarassati, Paulo ^{[1
]}

Jalalian, Nazli ^{[1
,2
]}

Olofsson, Berit ^{[2
]}

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

机构：

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

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

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 43期

基金：

巴西圣保罗研究基金会;

关键词：

Rearrangement; Hypervalent iodine; Ring contraction; Oxidation; Alkenes; DIASTEREOSELECTIVE TOTAL-SYNTHESIS; MEDIATED RING CONTRACTION; FLUORINATED ALCOHOLS; ACID; 1,2-DIHYDRONAPHTHALENES; DERIVATIVES; CHEMISTRY; EXPANSION; ALDEHYDES; EPOXIDES;

D O I：

10.1016/j.tetlet.2013.08.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel protocol for the oxidative rearrangement of alkenes using in situ generated hypervalent iodine(III) was developed. This approach uses inexpensive, readily available, and stable chemicals (PhI, mCPBA, and TsOH) giving rearrangement products in yields comparable to those obtained using the more expensive commercially available [hydroxy(tosyloxy)iodo]benzene [HTIB or Koser's reagent]. Additionally, an alternative protocol for the synthesis of 1-methyl-2-tetralone through the one-step epoxidation/rearrangement of 4-methyl-1,2-dihydronaphthalene using mCPBA and TsOH was developed. (c) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5818 / 5820

页数：3

共 56 条

[1] Synthesis of Chromanes and 4H-Chromenes: Exploring the Oxidation of 2H-Chromenes and Dihydro-1-benzoxepines by Hypervalent Iodine(III) [J].

Ahmad, Anees ;

Silva, Luiz F., Jr. .

SYNTHESIS-STUTTGART, 2012, 44 (23) :3671-3677

[2] Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones [J].

Anderson, AM ;

Blazek, JM ;

Garg, P ;

Payne, BJ ;

Mohan, RS .

TETRAHEDRON LETTERS, 2000, 41 (10) :1527-1530

[3]

[Anonymous], 2003, TOPICS CURRENT CHEM

[4] EFFECT OF RING SIZE AND METHYL SUBSTITUENTS ON LIBR-CATALYZED REARRANGEMENTS OF ARYLOXIRANES [J].

BANKS, H ;

ZIFFER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3743-3747

[5] Fluorinated alcohols:: A new medium for selective and clean reaction [J].

Bégué, JP ;

Bonnet-Delpon, D ;

Crousse, B .

SYNLETT, 2004, (01) :18-29

[6] A Ring Contraction Strategy toward a Diastereoselective Total Synthesis of (+)-Bakkenolide A [J].

Carneiro, Vania M. T. ;

Ferraz, Helena M. C. ;

Vieira, Tiago O. ;

Ishikawa, Eloisa E. ;

Silva, Luiz F., Jr. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :2877-2882

[7] Versatile hypervalent-iodine(III)-catalyzed oxidations with m-chloroperbenzoic acid as a cooxidant [J].

Dohi, T ;

Maruyama, A ;

Yoshimura, M ;

Morimoto, K ;

Tohma, H ;

Kita, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6193-6196

[8] Discovery of Stabilized Bisiodonium Salts as Intermediates in the Carbon-Carbon Bond Formation of Alkynes [J].

Dohi, Toshifumi ;

Kato, Daishi ;

Hyodo, Ryo ;

Yamashita, Daisuke ;

Shiro, Motoo ;

Kita, Yasuyuki .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (16) :3784-3787

[9] Fluoroalcohols: versatile solvents in hypervalent iodine chemistry and syntheses of diaryliodonium(III) salts [J].

Dohi, Toshifumi ;

Yamaoka, Nobutaka ;

Kita, Yasuyuki .

TETRAHEDRON, 2010, 66 (31) :5775-5785

[10] The synthesis and rearrangement of some decahydro- and tetrahydronaphthalenediols [J].

English, J ;

Cavaglieri, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1085-1089

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