Tandem catalysis in the polycyclisation of dienes to produce multi-substituted tetrahydrofurans

被引：5

作者：

Donohoe, Timothy J. ^{[1
]}

Lindsay-Scott, Peter J. ^{[1
]}

Parker, Jeremy S. ^{[2
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

[2] AstraZeneca, Proc R&D Avlon Charnwood, Avlon Works, Bristol BS10 7ZE, Avon, England

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 26期

基金：

英国工程与自然科学研究理事会;

关键词：

Tandem catalysis; Oxidation; Osmium; Polycyclisation; TETHERED AMINOHYDROXYLATION TA; OXIDATIVE CYCLIZATION; OSMIUM-TETROXIDE; 1,5-DIENES; DIHYDROXYLATION;

D O I：

10.1016/j.tetlet.2009.03.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new catalytic protocol has been established by using two separate oxidation reactions, catalysed by osmium, in tandem. Control of the pH and oxidation state of the metal is crucial in controlling this new sequence, which begins with a tethered aminohydroxylation reaction (Os(VIII) is active) and is followed by an oxidative cyclisation under acidic conditions (Os(VI) is active). The result of this work is an extremely quick route (five steps from commercially available materials) to complex THF rings containing an adjacent oxazolidinone and four new stereogenic centres. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3523 / 3526

页数：4

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