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- W1976336687 abstract "A novel Pd-catalyzed reaction of a 2-halo- or 2-trifloxy-l, 3-butadiene derivative with a soft nucleophile is developed. The reaction proceeds via an exo-alkylidene-π-allylpalladium intermedi-ate in a formal SN2' fashion to give an allenic compound exclusively. A variety of soft nucleophiles, such as malonates, phenoxides, and imides, are applicable to the reaction, and thus a wide range of functionality can be introduced to the products. The reaction is extended into an asymmetric counterpart and axially chiral allenes are prepared with up to 93% ee by the use of chiral palladium catalysts. A formal total synthesis of an insect pheromone is achieved using the Pd-catalyzed asymmetric reaction as a key step. The Pd-catalyzed reaction also enables to prepare axially chiral (allenylmethyl) silanes and allenylsilanes in optically active forms. Reactions of these silylallenes with appropriate electrophiles proceed via SE', pathways and the allenic axial chirality is efficiently transferred to stereogenic carbon centers in the SE', products." @default.
- W1976336687 created "2016-06-24" @default.
- W1976336687 creator A5025022119 @default.
- W1976336687 date "2008-07-08" @default.
- W1976336687 modified "2023-09-23" @default.
- W1976336687 title "ChemInform Abstract: Palladium-Catalyzed Stereoselective Synthesis of Multisubstituted Allenes and Their Application in Organic Transformations" @default.
- W1976336687 cites W2950478135 @default.
- W1976336687 doi "https://doi.org/10.1002/chin.200828256" @default.
- W1976336687 hasPublicationYear "2008" @default.
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