51978-98-4Relevant articles and documents
Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions
Disetti, Paolo,Moccia, Maria,Salazar Illera, Diana,Suresh, Surisetti,Adamo, Mauro F. A.
supporting information, p. 10609 - 10612 (2015/11/17)
The reaction between 3-methyl-4-nitro-5-styrylisoxazoles and ethyl isocyanoacetate proceeded under phase transfer catalysis to give enantioenriched monoadducts in high enantiomeric excess (up to 99% ee). The resulting adducts were subsequently cyclised to give 2,3-dihydropyrroles and substituted pyrrolidines in identical high ees and as a single diastereoisomer.
Catalytic asymmetric conjugate addition of nitroalkanes to 4-nitro5-styrylisoxazoles
Baschieri, Andrea,Bernardi, Luca,Ricci, Alfredo,Suresh, Surisetti,Adamo, Mauro F. A.
supporting information; body text, p. 9342 - 9345 (2010/03/24)
(Chemical equation presented) Nitro versus nitro: 4-Nitro-5- styrylisoxazoles were used as masked α,β-unsaturated carboxylic acids in the titled catalytic asymmetric transformation. The 4-nitroisoxazole core acts as an activator of the conjugated alkene and a latent carboxylate functionality. The reaction proceeded with 5 mol% of a readily prepared phasetransfer catalyst at room temperature with remarkable diastereo- and enantioselectivity (see scheme).