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Synlett 2015; 26(11): 1528-1532
DOI: 10.1055/s-0034-1380290
DOI: 10.1055/s-0034-1380290
letter
Asymmetric Synthesis of Tertiary α-Hydroxy Phosphonic Acid Derivatives under Aerobic Oxidation Conditions
Further Information
Publication History
Received: 20 January 2015
Accepted after revision: 11 February 2015
Publication Date:
05 March 2015 (online)
This manuscript is dedicated to Peter Vollhardt, who launched SYNLETT 25 years ago and since then has continuously served in a number of important editorial capacities.
Abstract
The copper-catalyzed asymmetric α-hydroxylation of β-ketophosphonates, using in situ generated nitrosocarbonyl compounds as electrophilic source of oxygen, is reported. The reaction merges aerobic oxidation and Lewis acid catalysis. α-Aminoxy-β-ketophosphonates were synthesized in high yields (up to 97% yield) and high enantioselectivities (up to >99% ee).
Key words
nitrosocarbonyl compounds - copper - bisoxazoline - α-hydroxy phosphonic acid - aerobic oxidationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380290.
- Supporting Information
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