Diels-Alder reactivity of trialkyl 2-phosphonoacrylates with N-buta-1,3-dienylsuccinimide
(1997) Royal Society of Chemistry. Journal: Perkin Transactions 2 — n° 10, p. 1965-1968 (1997)
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- Abstract
- 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.
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Defacqz, N., Touillaux, R., Tinant, B., Declercq, J.-P., Peeters, D., & Marchand-Brynaert, J. (1997). Diels-Alder reactivity of trialkyl 2-phosphonoacrylates with N-buta-1,3-dienylsuccinimide. Royal Society of Chemistry. Journal: Perkin Transactions 2, 10, 1965-1968. https://doi.org/10.1039/a702324c (Original work published 1997)