Prenyl carbamates: preparation and deprotection | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

1155649

Reference Type

Journal Article

Title

Prenyl carbamates: preparation and deprotection

Author(s)

Vatele, JM

Year

2004

Is Peer Reviewed?

Journal

Tetrahedron
ISSN: 0040-4020

Publisher

PERGAMON-ELSEVIER SCIENCE LTD

Location

OXFORD

Volume

Issue

Page Numbers

4251-4260

Language

English

DOI

10.1016/j.tet.2004.03.028

Web of Science Id

WOS:000221133700016

URL

https://linkinghub.elsevier.com/retrieve/pii/S004040200400403X
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Abstract

Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

Keywords

amines; carbamates; iodine; prenylation; protecting groups