Structurally Defined α-Tetralol-Based Chiral Hypervalent Iodine Reagents

被引：13

作者：

Hokamp, Tobias ^{[1
]}

Wirth, Thomas ^{[1
]}

机构：

[1] Cardiff Univ, Sch Chem, Main Bldg,Pk Pl, Cardiff CF10 3AT, S Glam, Wales

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 13期

关键词：

KETONES; SPIROLACTONIZATION; DEAROMATIZATION; REARRANGEMENTS; DIAMINATION; CATALYSIS; TOSYLOXYLATION; HYDROGENATION; OXIDATION; SALTS;

D O I：

10.1021/acs.joc.9b01315

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel class of chiral hypervalent iodine reagents containing an a-tetralol scaffold is introduced. Iodine triacetate is employed in a key step as a highly selective and efficient iodinating reagent for a short and convenient synthesis of iodine(III) derivatives. Solid-state X-ray analyses offer valuable structural information, while reactivities and stereoselectivities are investigated in three model reactions.

引用

页码：8674 / 8682

页数：9

共 76 条

[1] Vicinal Difunctionalization of Alkenes under Iodine(III) Catalysis involving Lewis Base Adducts [J].

Aertker, Kristina ;

Rama, Raquel J. ;

Opalach, Julita ;

Muniz, Kilian .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (08) :1290-1294

[2] Catalytic Enantioselective α-Oxysulfonylation of Ketones Mediated by Iodoarenes [J].

Altermann, Sabine M. ;

Richardson, Robert D. ;

Page, T. Keri ;

Schmidt, Ruth K. ;

Holland, Edward ;

Mohammed, Umal ;

Paradine, Shauna M. ;

French, Andrew N. ;

Richter, Christine ;

Bahar, A. Masih ;

Witulski, Bernhard ;

Wirth, Thomas .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) :5315-5328

[3] New chiral hypervalent iodine(V) compounds as stoichiometric oxidants [J].

Altermann, Sabine M. ;

Schaefer, Sascha ;

Wirth, Thomas .

TETRAHEDRON, 2010, 66 (31) :5902-5907

[4]

[Anonymous], 2018, ANGEW CHEM

[5]

[Anonymous], 2009, Angew. Chem

[6]

[Anonymous], 2012, ANGEW CHEM-GER EDIT, DOI DOI 10.1002/ANGE.201107703

[7]

[Anonymous], 2016, ANGEW CHEM, DOI DOI 10.1002/ANGE.201507180

[8]

[Anonymous], 2014, ANGEW CHEM, DOI DOI 10.1002/ANGE.201400405

[9]

[Anonymous], 2013, ANGEW CHEM, DOI DOI 10.1002/ANGE.201302358

[10]

[Anonymous], 2010, ANGEW CHEM

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