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- W3204856540 abstract "Lewis-acid mediated allylations of β-alkoxy N-tosyl imines lead to 3-alkoxy homoallylic N-tosyl amines with anti diastereoselectivity. Diastereoselectivity and yields of reactions are comparable between two methods of Hosomi-Sakurai allylations. Observed selectivity trends and computational evidence suggest that 1,3 asymmetric induction occurs through the formation of a six- membered ring chelate which adopts a half-chair-like conformation. The product ratios of allylations to β-alkoxy N-tosyl imines are dependent on conformation preferences of the chelate and stereoelectronic interactions in the transition-state structures. Debenzylation and detosylation of these allylation products result in anti 1,3-amino alcohols, a privileged motif in synthetic and natural bioactive compounds." @default.
- W3204856540 created "2021-10-11" @default.
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- W3204856540 date "2021-09-29" @default.
- W3204856540 modified "2023-09-27" @default.
- W3204856540 title "1,3-Asymmetric Induction in Diastereoselective Allylations of Chiral N-Tosyl Imines" @default.
- W3204856540 doi "https://doi.org/10.33774/chemrxiv-2021-df4ns" @default.
- W3204856540 hasPublicationYear "2021" @default.
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