Dual stereocontrol in aldol reactions catalysed by hydroxyproline derivatives in the presence of a large amount of water

Gurka, András A.; Szőri, Kornél; Bartók, Mihály; London, Gábor

doi:10.1016/j.tetasy.2016.08.009

Cited by 10 publications

(2 citation statements)

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“…In the presence of ammonium chloride ( R )- 98 was obtained in 58% ee, whereas in the presence of NaOAc its enantiomer was formed in only 20% ee (Scheme ). This methodology was further studied with different aromatic aldehydes . The formation of a biphasic micellar system in the aqueous media seems to be crucial for the observed enantioselectivities.…”

Section: Stereodivergence In Acyclic Systemsmentioning

confidence: 99%

“…102 This methodology was further studied with different aromatic aldehydes. 103 The formation of a biphasic micellar system in the aqueous media seems to be crucial for the observed enantioselectivities. Substrate-dependent reversal of the enantioselectivity has been found in the aldol reaction of acetone with isatins 99 catalyzed by L-Pro.…”

Section: Chemical Reviewsmentioning

confidence: 99%

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Stereodivergent Catalysis

2018

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This review covers diastereo- and enantiodivergent catalyzed reactions in acyclic and cyclic systems using metal complexes or organocatalysts. Among them, nucleophilic addition to carbon-carbon and carbon-nitrogen double bonds, α-functionalization of carbonyl compounds, allylic substitutions, and ring opening of oxiranes and aziridines are considered. The diastereodivergent synthesis of alkenes from alkynes is also included. Finally, stereodivergent intramolecular and intermolecular cycloadditions and other cyclizations are also reported.

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Section: Stereodivergence In Acyclic Systemsmentioning

confidence: 99%

Section: Chemical Reviewsmentioning

confidence: 99%