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Synthesis 2018; 50(04): 846-852
DOI: 10.1055/s-0036-1591742
paper
© Georg Thieme Verlag Stuttgart · New York

Practical and Scalable Synthesis of 7-Azetidin-1-yl-4-(hydroxy­methyl)coumarin: An Improved Photoremovable Group

Giovanni Bassolino
Laboratorium für Organische Chemie, ETH Zürich, HCI G329, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: pablo.rivera-fuentes@org.chem.ethz.ch
,
Elias A. Halabi
Laboratorium für Organische Chemie, ETH Zürich, HCI G329, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: pablo.rivera-fuentes@org.chem.ethz.ch
,
Pablo Rivera-Fuentes  *
Laboratorium für Organische Chemie, ETH Zürich, HCI G329, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland   Email: pablo.rivera-fuentes@org.chem.ethz.ch
› Author AffiliationsThis work was supported by the Swiss National Science Foundation (grant 200021_165551).
Further Information

Publication History

Received: 25 October 2017

Accepted after revision: 27 November 2017

Publication Date:
21 December 2017 (online)

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Published as part of the Bürgenstock Special Section 2017 Future­ Stars in Organic Chemistry

Abstract

7-Substituted 4-methylcoumarin derivatives are widely employed as photoprotecting groups in chemistry and biology. We have recently shown that the 7-azetidinylated version of this photocage releases carboxylic acids in aqueous solution more efficiently than the traditionally used 7-diethylamino variant. Here we present a robust and scalable route to prepare the 7-azetidinylated alcohol, a useful precursor for the photoprotection of a variety of leaving groups, and its use in the preparation of model phosphate, sulfonate, and carbamate derivatives.

Keywords

azetidine - bioorganic chemistry - chromophores - photochemistry - protecting groups - uncaging

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591742.
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