Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 22, Pages 9472-9477Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201932m
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Funding
- Direccion General de Investigacion del Ministerio de Ciencia e Innovacion (MCINN, Madrid DGI) [CTQ2009-12156BQU]
- Universidad del Pais Vasco - Departamento de Educacion Universidades e Investigacion of Gobierno Vasco [GIU/09/57, IT-422-10]
- Ministerio de Educacion (Madrid)
- European Social Found
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A simple and efficient selective synthesis of 1H-pyrrole-2-phosphine oxides 3 and -phosphonates 7 by addition of enolates derived from acetyl acetates to 2H-azirinylphosphine oxide 1 and -phosphonate 6 is reported. Nucleophilic addition of enolates derived from diethyl malonate to 2H-azirines 1 and 6 led to the formation of functionalized 2-hydroxy-1H-pyrrole-5-phosphine oxide 9 and -phosphonate 10, while vinylogous alpha-aminoalkylphosphine oxides 14 and -phosphonate 15 may be obtained from azirines and the enolate derived from diethyl 2-phenylmalonate. Ring closure of vinylogous derivatives 14 and 15 in the presence of base led to the formation of 1,5-dihydro-3-pyrrolin-2-ones containing a phosphine oxide 17 or a phosphonate group 18.
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