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- W2949277904 abstract "Palladium catalyzed intramolecular [3 + 2] cycloadditions of diastereomerically pure methylenecyclopropanes MCPs have been investigated. The reaction was found to be stereospecific and occurred with retention of configuration at the carbon center undergoing reaction. A variety of substitution patterns were tolerated on and around the MCP. Deuterium labeling studies have been conducted, and information about the rate of the reaction was obtained. A mechanism has been proposed involving π-allyl intermediates. Pd2(dba)3/P(OiPr)3 was a suitable catalyst for most cycloadditions, but molecular sieves or Pd(PPh3)4 improved the reaction with some substrates. 1,4-Addition of hydride or a carbanion to the enoate was achieved with high selectivity at the newly formed stereocenter. The allylic alcohol was selectively epoxidized with VO(acac)2/t-BuOOH." @default.
- W2949277904 created "2019-06-27" @default.
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- W2949277904 date "1996-01-01" @default.
- W2949277904 modified "2023-10-17" @default.
- W2949277904 title "Transition Metal Catalyzed Stereospecific Intramolecular [3 + 2] Cycloadditions of Methylenecyclopropanes with Alkynes" @default.
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- W2949277904 doi "https://doi.org/10.1021/ja9611809" @default.
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