2015
DOI: 10.1016/j.tetasy.2015.08.011
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The 2′-phenyl cinchonidine thiourea-catalyzed asymmetric addition of alcohols to isatin-derived N-Boc ketimines

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Cited by 19 publications
(5 citation statements)
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“…5 The chiral 3-substituted 3-aminooxindole skeleton is present in a variety of biologically significant compounds, 6 and enantioselective addition of oxygen-based nucleophiles to isatin-derived ketimines represents a straightforward and convenient route for the formation of chiral quaternary N,O-acetals at the C3 position of the 2-oxindoles. Excellent results in organocatalytic asymmetric reactions have been achieved by Wu et al (Scheme 1a), 7 Zhou et al (Scheme 1b), 8 Nakamura et al (Scheme 1c), 9 Li et al (Scheme 1d) 10 and Shi et al…”
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confidence: 93%
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“…5 The chiral 3-substituted 3-aminooxindole skeleton is present in a variety of biologically significant compounds, 6 and enantioselective addition of oxygen-based nucleophiles to isatin-derived ketimines represents a straightforward and convenient route for the formation of chiral quaternary N,O-acetals at the C3 position of the 2-oxindoles. Excellent results in organocatalytic asymmetric reactions have been achieved by Wu et al (Scheme 1a), 7 Zhou et al (Scheme 1b), 8 Nakamura et al (Scheme 1c), 9 Li et al (Scheme 1d) 10 and Shi et al…”
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confidence: 93%
“…aUnless otherwise noted, all reactions were performed with isatin-derived N -Boc ketimine 1 (0.15 mmol), alcohols 2 (1.5 mmol), DIPEA (0.015 mmol), L5 (10 mol%), and Zn(ClO 4 ) 2 ·6H 2 O (10 mol%) in dry CH 2 Cl 2 (2.0 mL) at room temperature for 24 h.bIsolated yields.cThe ee values were determined by HPLC.dAbsolute configuration was tentatively deduced by comparison with the reported sign of specific rotation of the product. 8 Others were assigned by analogy.…”
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confidence: 99%
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“…[69] The construction of optically active isatin-derived N,O-aminals was described in the presence quininebased catalyst. [70] The nucleophilic addition of alcohols to isatin derived N-Boc ketimines gave N,O-aminals containing a quaternary stereocenter in moderate to excellent stereoselectivities and yields (Scheme 31).…”
Section: Intermolecular Reactions With O-nucleophilesmentioning
confidence: 99%
“…Here also, catalyst VI blocks the Re face of the enone, and thus Michael addition takes place from the Si face to generate product 3a. Since the hemiaminal chiral center is stable, 15 the diastereoselectiviity of this reaction might be due to the aza-Michael step. In summary, this report delineates the first organocatalytic asymmetric synthesis of spirooxindole embedded oxazolidines.…”
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confidence: 99%