Convenient preparations of 2,3-dihydro-4H-pyran-4-ones from D-glucal triacetate: Selective oxidations of allylic acetates and allylic silyl ethers using N-bromosuccinimide

Article abstract of DOI:10.1080/00397919308018600

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.

Full text of DOI:10.1080/00397919308018600

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Synthetic Communications: An
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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
a
a
a
Anne Bouillot , Duc Do Khac , Marcel Fétizon , Frédéric
a
a
Guir & Yvone Memoria
a
Laboratoire de Synthése Organique , Ecole Polytechnique ,
F. 91128, PALAISEAU Cedex
Published online: 23 Sep 2006.
To cite this article: Anne Bouillot , Duc Do Khac , Marcel Fétizon , Frédéric Guir &
Yvone Memoria (1993) 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, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 23:15, 2071-2081, DOI:
10.1080/00397919308018600
To link to this article: http://dx.doi.org/10.1080/00397919308018600
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