Scope and stereochemical course of the addition of (trimethylsilyl)allenes to ketones and aldehydes. A regiocontrolled synthesis of homopropargylic alcohols

Rick L. Danheiser, David J. Carini, Carrie A. Kwasigroch
J. Org. Chem., 1986, 51 (20), pp 3870–3878
DOI: 10.1021/jo00370a023
Publication Date: October 1986
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      A novel transition metal-catalyzed rearrangement of silylated cyclopropenes to the corresponding allenes is described. The presence of both the trimethylsily group on the cyclopropene and platinum catalyst are crucial for this rearrangement.

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      Stepwise application of the Pd-catalyzed SN2′ reaction and the desilylative SE2′ reaction to the ambivalent 2-bromo-1-silyl-1,3-dienes provides a novel route to the highly enantioselective construction of tertiary and quaternary propargylic stereogenic ...

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  • Published In Issue October, 1986

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