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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 15
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Original Articles

Convenient Preparations of 2,3-Dihydro-4H-pyran-4-ones from D-Glucal Triacetate : Selective Oxidations of Alyllic Acetates and Allylic Silyl Ethers Using N-Bromosuccinimide

Anne Bouillot Laboratoire de Synthése Organique, Ecole Polytechnique, F. 91128, PALAISEAU Cedex
,
Duc Do Khac Laboratoire de Synthése Organique, Ecole Polytechnique, F. 91128, PALAISEAU Cedex
,
Marcel Fétizon Laboratoire de Synthése Organique, Ecole Polytechnique, F. 91128, PALAISEAU Cedex
,
Frédéric Guir Laboratoire de Synthése Organique, Ecole Polytechnique, F. 91128, PALAISEAU Cedex
&
Yvone Memoria Laboratoire de Synthése Organique, Ecole Polytechnique, F. 91128, PALAISEAU Cedex
Pages 2071-2081 | Received 25 Feb 1993, Published online: 23 Sep 2006
 
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Abstract

N-Bromosuccinimide (1.1 eq) in the presence of potassium carbonate (2 eq) and a catalytic amount of dibenzoyl peroxide converts the allylic acetates and the allylic silyl ethers (O-TBDMS or O-SiEt3) of secondary allylic alcohols, derived from D-glucal 3a into corresponding dihydro γ-pyrones 2.

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