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Metal-free photosensitized oxyimination of unactivated alkenes with bifunctional oxime carbonates

Patra, Tuhin, Das, Mowpriya, Daniliuc, Constantin G. and Glorius, Frank 2021. Metal-free photosensitized oxyimination of unactivated alkenes with bifunctional oxime carbonates. Nature Catalysis 4 (1) , pp. 54-61. 10.1038/s41929-020-00553-2

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Abstract

The 1,2-aminoalcohol motif is one of the most prevalent structural components found in high-value organic molecules, including pharmaceuticals and natural products. Generally, its preparation requires pre-functionalized substrates and manipulations of one functional group at a time to achieve the desired regioisomer. Herein, we describe a metal-free photosensitization protocol for the installation of both amine and alcohol functionalities into alkene feedstocks in a single step. This approach is enabled by the identification of oxime carbonate as a suitable bifunctional source of both oxygen- and nitrogen-centred radicals for addition across alkenes with complementary regioselectivity compared to Sharpless aminohydroxylation. Use of orthogonal protection for amine and alcohol functionalities enables the direct synthe

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Nature Research
ISSN: 2520-1158
Date of First Compliant Deposit: 11 February 2021
Date of Acceptance: 12 November 2020
Last Modified: 06 Oct 2021 13:58
URI: https://orca.cardiff.ac.uk/id/eprint/138477

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