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One-pot diastereoselective synthesis of densely functionalized 2H-indeno[2,1-b]furans. Single-crystal X-ray structure of dimethyl 8,8a-dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno[2,1-b]furan- 2,3-dicarboxylate.
Autorzy
Rok wydania
2008
Czasopismo
Numer woluminu
91
Strony
2252-2261
DOI
10.1002/hlca.200890245
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Highly reactive 1 : 1 intermediates were produced in the reaction of Ph3P and dialkyl acetylenedicarboxylates (=dialkyl but-2-ynedioates). Protonation of these intermediates by alcohols (2,2,2-trichloroethanol, propargyl alcohol (=prop-2-yn-1-ol), MeOH, benzyl alcohol, and allyl alcohol (=prop-2-en-1-ol) led to vinyltriphenylphosphonium salts 4, which underwent a Michael addition reaction with the conjugate base to produce the corresponding stabilized phosphonium ylides 5 (Scheme). Wittig reaction of the stabilized phosphonium ylides with ninhydrin (6) led to the corresponding densely functionalized 2H-indeno[2,1-b]furans 10 in fairly good yields (Table 1). The structures of the final products were confirmed by IR, 1H- and 13C-NMR spectroscopy, and mass spectrometry. The configuration of dimethyl 8,8a-dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno[2,1-b]furan-2,3-dicarboxylate (10a) was established by a single-crystal X-ray structure determination, establishing that the one-pot multicomponent condensation reaction was completely diastereoselective.
Adres publiczny
https://doi.org/10.1002/hlca.200890245
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