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DOI: 10.1055/s-0036-1591742
Practical and Scalable Synthesis of 7-Azetidin-1-yl-4-(hydroxymethyl)coumarin: An Improved Photoremovable Group
This work was supported by the Swiss National Science Foundation (grant 200021_165551).Publication History
Received: 25 October 2017
Accepted after revision: 27 November 2017
Publication Date:
21 December 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201804/lookinside/thumbnails/ss-2017-z0688-op_10-1055_s-0036-1591742-1.jpg)
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 - uncagingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591742.
- Supporting Information
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