Asymmetric Hydroxylative Phenol Dearomatization through In Situ Generation of Iodanes from Chiral Iodoarenes and m-CPBA

被引：238

作者：

Quideau, Stephane ^{[1
]}

Lyvinec, Gildas ^{[1
]}

Marguerit, Melanie ^{[1
]}

Bathany, Katell ^{[1
]}

Ozanne-Beaudenon, Aurelie ^{[1
]}

Buffeteau, Thierry ^{[1
]}

Cavagnat, Dominique ^{[1
]}

Chenede, Alain ^{[2
]}

机构：

[1] CNRS, UMR 5255, Inst Europeen Chim & Biol, Inst Mol Sci, F-33607 Pessac, France

[2] Simafex, F-17230 Marans, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 25期

关键词：

asymmetric synthesis; dearomatization; hypervalent compounds; iodine; vibrational circular dichroism; M-CHLOROPERBENZOIC ACID; 2-IODOXYBENZOIC ACID; OXIDATIVE DEAROMATIZATION; ORTHOQUINONE MONOKETALS; ALPHA-ACETOXYLATION; CIRCULAR-DICHROISM; SAFE OXIDATION; HYPERVALENT; REACTIVITY; KETONES;

D O I：

10.1002/anie.200901039

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

'I' is all the hype: A twofold excess of iodoarene in the title reaction leads to ortho-quinols in good yields, whereas organocatalytic versions of this reaction enable subsequent epoxidation in a regio- and diastereoselective fashion. Chiral iodobiarenes led to enantioselectivities up to 50 % ee. m-CPBA=meta-chloroperoxybenzoic acid. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4605 / 4609

页数：5

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