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  4. Practical Palladium-Mediated Deprotective Method of Allyloxycarbonyl Groups in Aqueous Media
 
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research article

Practical Palladium-Mediated Deprotective Method of Allyloxycarbonyl Groups in Aqueous Media

Genêt, Jean-Pierre
•
Blart, Erol
•
Savignac, Monique
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1993
Tetrahedron

The Allyloxycarbonyl (Alloc) moiety can be removed smoothly and selectively in good yield (73-100%) from allylic eaters, carbamates and carbonates by aqueous Pd (0) catalyzed allyl transfer to diethylamine in aqueous media employing a water soluble phosphine. The allyl scavenger as well as by product allyl diethylamine are volatile and easily removed in vacuo. In a two phase system an increased selectivity is seen. The method has been successfully used for deprotection of a wide range of secondary amines or base sensitive derivatives and the catalyst is efficiently recycled.

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Type
research article
DOI
10.1016/S0040-4020(01)80771-7
Author(s)
Genêt, Jean-Pierre
•
Blart, Erol
•
Savignac, Monique
•
Lemeune, Sylvain
•
Lemaire-Audoire, Sandrine
•
Paris, Jean-Marc
•
Bernard, Jean-Marie
Date Issued

1993

Published in
Tetrahedron
Volume

50

Issue

2

Start page

497

End page

503

Subjects

carboxy-protecting group

•

peptide-synthesis

•

allyl

•

cleavage

Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LGSA  
Available on Infoscience
June 16, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/231894
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