✍ Scribed by Nobuyuki Mase; Shutaro Wake; Yoshihiko Watanabe; Takeshi Toru
No coin nor oath required. For personal study only.
The reaction of (2S,Ss)-0t-(I-hydroxyethyl)vinyl sulfoxide with alkyl radicals and tributyltin hydride gave the addition-hydrogenation products with high diastereoselectivity, whereas (2R,Ss)-~-( Ihydroxyethyl)vinyl sulfoxide gave no products under similar conditions. An important role of intramolecular hydrogen bonding for the diastereoselectivity as well as the reactivity toward alkyl radicals is discussed.
📜 SIMILAR VOLUMES
Radical addition to a glyoxylic oxime ether was accomplished under mild conditions using an alkyl radical generated from a free carboxylic acid via photochemical decarboxylation. The photoreaction provided an efficient route to a-substituted a-aminoesters from carboxylic acids and oxime ether.
and treated with lBuCl (1.18 g, 12.8 mmol) directly after filtration. The mixture was stirred at room temperature for 12 h before the orange solution was evaporated to dryness. Recrystallization of the residue from toluene (ca. 30 mL) affords a yellow crystalline powder (2.50 g, 40%). which decompos