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• W2079745101 endingPage "4963" @default.
• W2079745101 startingPage "4952" @default.
• W2079745101 abstract "The SmI2-mediated radical coupling reactions of β-hydroxylated pyrrolidine/piperidine aza-hemiacetals 8 and 9 and N,S-acetals 6 and 33 with α,β-unsaturated compounds are described. This method allows a rapid access to β-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N,S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A2 (2), uniflorine A (3, 6-epi-casuarine), and the unnatural epimer 7-epi-casuarine (37) have been synthesized in four and five steps with overall yields of 34%, 16%, and 13%, respectively. The radical mechanism of the coupling reactions has been confirmed by controlled experiments, which also allowed deducing the anionic mechanism in the coupling between N,S-acetal 6 and carbonyl compounds. This demonstrates that the mechanisms of these SmI2-mediated reactions are switchable from Barbier-type anionic to radical by cooperative action of BF3·OEt2 and t-BuOH." @default.
• W2079745101 created "2016-06-24" @default.
• W2079745101 creator A5025223478 @default.
• W2079745101 creator A5026341515 @default.
• W2079745101 creator A5043167977 @default.
• W2079745101 creator A5048553281 @default.
• W2079745101 creator A5057538068 @default.
• W2079745101 creator A5086854297 @default.
• W2079745101 date "2011-05-26" @default.
• W2079745101 modified "2023-10-10" @default.
• W2079745101 title "SmI₂-Mediated Radical Cross-Couplings of α-Hydroxylated Aza-hemiacetals and <i>N</i>,<i>S</i>-Acetals with α,β-Unsaturated Compounds: Asymmetric Synthesis of (+)-Hyacinthacine A₂, (−)-Uniflorine A, and (+)-7-<i>epi</i>-Casuarine" @default.
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