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[4+2] Cycloaddition of 1-aminodienes and 2-substituted vinylphosphonates: application to asymmetric synthesis of 3-amino-5-phosphono-1-cyclohexene derivatives

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Robiette, Raphaël [UCL] Defacqz, N Stofferis, J Marchand-Brynaert, Jacqueline [UCL]

N-Butadienylsuccinimide (1), iso-propyl N-butadienyl-(S)-pyroglutamate (5) and N-butadienyl-(R)-4-phenyloxazolidin-2-one (6) reacted with vinylphosphonates, vicinally-substituted (2) by electronwithdrawing groups (CO2Me, CN, COMe), to furnish [4+2] cycloadducts (3-4,7-10, and 11-14) in moderate to good yields (40-88%). The reactions were highly selective: regioselectivity of 95-100%, endoselectivity of 75-92% and facial selectivity of 80-95%. The major diastereoisomers were fully characterized by H-1 and C-13 NMR spectroscopy. (C) 2003 Elsevier Science Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2003
Language Anglais
Journal information "Tetrahedron" - Vol. 59, no. 23, p. 4167-4175 (2003)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4020
e-issn 1464-5416
Publication status Publié
Affiliation UCL
Keywords Diels-Alder cycloaddition ; chiral 1-aminodiene ; vinylphosphonate ; asymmetric synthesis ; gamma-aminophosphonic derivatives
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Bibliographic reference Robiette, Raphaël ; Defacqz, N ; Stofferis, J ; Marchand-Brynaert, Jacqueline. [4+2] Cycloaddition of 1-aminodienes and 2-substituted vinylphosphonates: application to asymmetric synthesis of 3-amino-5-phosphono-1-cyclohexene derivatives. In: Tetrahedron, Vol. 59, no. 23, p. 4167-4175 (2003)
Permanent URL http://hdl.handle.net/2078.1/40981