Defacqz, Nathalie
[UCL]
Touillaux, Roland
[UCL]
Tinant, Bernard
[UCL]
Declercq, Jean-Paul
[UCL]
Peeters, Daniel
[UCL]
Marchand-Brynaert, Jacqueline
[UCL]
N-Buta-1,3-dienylsuccinimide 1 reacts quantitatively with trimethyl 2-phosphonoacrylate 2a to furnish the ortho-[4 + 2]-cycloadduct 3a as a single stereoisomer. The cis axial/equatorial. relationship between the succinimido and phosphonate groups respectively has been established by NMR and X-ray diffraction analyses. Triethyl 2-phosphonoacrylate 2b similarly undergoes cycloaddition with the diene 1 to give a 55:45 mixture of ortho stereoisomers 3b (cia axial/equatorial) and 4b (trans axial/axial). The activating and directing effect of the phosphonate group is discussed on the basis of a theoretical approach considering the van der Waals complexes.
Bibliographic reference |
Defacqz, Nathalie ; Touillaux, Roland ; Tinant, Bernard ; Declercq, Jean-Paul ; Peeters, Daniel ; et. al. Diels-Alder reactivity of trialkyl 2-phosphonoacrylates with N-buta-1,3-dienylsuccinimide. In: Royal Society of Chemistry. Journal: Perkin Transactions 2, , no. 10, p. 1965-1968 (1997) |
Permanent URL |
http://hdl.handle.net/2078.1/45938 |