Issue 14, 2018
From the journal:

Green Chemistry

Cyclic allylic carbonates as a renewable platform for protecting chemistry in water†

Peter Olsén, ORCID logo *a   Jennifer Morvan,a   Supaporn Sawadjoon,a   Andrey Shatskiy,a   Eric V. Johnston ORCID logo *b  and  Björn Åkermark ORCID logo *a  

* Corresponding authors

a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
E-mail: polsen@kth.se, bjorn.akermark@su.se

b Sigrid Therapeutics AB, SE 111 52 Stockholm, Sweden
E-mail: eric@sigridthx.com

Abstract

The present work explores different cyclic allylic carbonates as a potential class of allylcarbamate precursors. The 5-membered carbonate formed a carbamate with very good thermal and pH stability, which could be cleanly deprotected in aqueous solution, in just 30 min with 2 mol% Pd(OAc)2 as catalyst. The polar nature of the installed motif made it possible to deprotect highly unpolar substrates in water as solvent.

Graphical abstract: Cyclic allylic carbonates as a renewable platform for protecting chemistry in water

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Article information

DOI
https://doi.org/10.1039/C8GC01622D
Article type
Communication
Submitted
23 May 2018
Accepted
06 Jun 2018
First published
14 Jun 2018
This article is Open Access
Creative Commons BY-NC license

Green Chem., 2018,20, 3186-3190

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Cyclic allylic carbonates as a renewable platform for protecting chemistry in water

P. Olsén, J. Morvan, S. Sawadjoon, A. Shatskiy, E. V. Johnston and B. Åkermark, Green Chem., 2018, 20, 3186 DOI: 10.1039/C8GC01622D

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