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- W2952019069 abstract "Umpolung in the allylation reaction is discussed with examples drawn from transi- tion-metal-catalyzed allylic substitution (with the allylic unit acting as an electrophile) and Lewis base-catalyzed allylation of aldehydes with allyltrichlorosilane (with the allyl acting as a nucleophile). Iridium-catalyzed electrophilic allylation of O-nucleophiles has been em- ployed in our new approach to C-nucleoside analogs, where the C-O bond (rather than C-C) was constructed stereospecifically. Variation of the absolute configuration in the starting seg- ments allowed the synthesis of all four combinations of D/L-α/β-ribosides. In the nucleophilic allylation of aldehydes, chiral pyridine-type N-oxide catalysts are presented, in particular QUINOX and METHOX, and the intriguing behavior of QUINOX is discussed. Here, the π-π interactions between the substrate aldehyde and the catalyst are suggested to rationalize the experimental observations. Good correlation between the calculated energies for the tran- sition states and the experimentally observed enantioselectivities has been obtained." @default.
- W2952019069 created "2019-06-27" @default.
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- W2952019069 date "2008-10-21" @default.
- W2952019069 modified "2023-09-27" @default.
- W2952019069 title "ChemInform Abstract: Asymmetric Synthesis: From Transition Metals to Organocatalysis" @default.
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- W2952019069 doi "https://doi.org/10.1002/chin.200843246" @default.
- W2952019069 hasPublicationYear "2008" @default.
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