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- W2082764470 abstract "A novel nucleophile, sulfonylimidate, has been successfully employed in Mannich-type reactions. Due to electron-withdrawing property of sulfonyl group of sulfonylimidate, the acidity of α-proton is enhanced so that sulfonylimidate bearing no activating functional group at α-position is deprotonated by relatively weak base. DBU-catalyzed reactions of sulfonylimidates with protected imines in DMF provided the adducts in high yields with high anti selectivity. This reaction represents a wide substrate scope and a high catalytic turnover. A thorough kinetic study revealed that rate-determining step is most likely deprotonation step in case of Ts-imidate. Alkali earth metal alkoxide and its HMDS salt also catalyze Mannich-type reactions of sulfonylimidates. The reactions catalyzed by Mg(O t Bu) 2 in DMF provided the adducts with high anti selectivity, while those catalyzed by [Sr(HMDS) 2 ] 2 gave syn selectivity. The asymmetric variant of Mannich-type reaction of sulfonylimidate was also achieved. Several transformations of sulfonylimidates to other functional groups were also demonstrated. Finally, direct-type catalytic formation of β-amino acid ester from aldehyde and sulfonylimidate was achieved via in situ formation of sulfonylimine and DBU-assisted hydrolysis of sulfonylimidate." @default.
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- W2082764470 date "2010-01-26" @default.
- W2082764470 modified "2023-10-16" @default.
- W2082764470 title "ChemInform Abstract: Catalytic Mannich-Type Reactions of Sulfonylimidates." @default.
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- W2082764470 doi "https://doi.org/10.1002/chin.201004041" @default.
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