Reaction of 2H-Azirine Phosphine Oxide and -Phosphonates with Nucleophiles. Stereoselective Synthesis of Functionalized Aziridines and α- and β-Aminophosphorus Derivatives

A simple and efficient stereoselective synthesis of aziridine-2-phosphonate 3, and -phosphine oxide 5 by diastereoselective addition of Grignard reagents to 2H-azirine phosphonate 1 and -phosphine oxide 4 is reported. Similarly, the addition of heterocyclic amines and benzenethiol to aziridines 1 an...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-10, Vol.70 (22), p.8895-8901
Main Authors: Palacios, Francisco, Ochoa de Retana, Ana M, Alonso, José M
Format: Article
Language:English
Subjects:
Amination
Aziridines - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Imidazoles - chemistry
Molecular Structure
Organic chemistry
Organophosphonates - chemistry
Phosphines - chemistry
Phthalimides - chemistry
Preparations and properties
Stereoisomerism
Sulfur - chemistry
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Summary:A simple and efficient stereoselective synthesis of aziridine-2-phosphonate 3, and -phosphine oxide 5 by diastereoselective addition of Grignard reagents to 2H-azirine phosphonate 1 and -phosphine oxide 4 is reported. Similarly, the addition of heterocyclic amines and benzenethiol to aziridines 1 and 4 yielded functionalized aziridines 10, 11, and 18. These aziridines are used as intermediates for the regioselective synthesis of β-aminophosphine oxides 6 and β-aminophosphonates 7, as well as α- aminophosphonates 8. Phenylsulfenyl-substituted α-aminophosphorus derivatives 15 and 19 are obtained directly from benzenethiol and 2H-azirine phosphonates 1 and -phosphine oxides 4.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051404i