α-(Disilylallenyl) α-amino acid derivatives from the Claisen rearrangement of propargyl glycinates Academic Article uri icon

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abstract

  • Silylpropargyl glycinate esters undergo [3,3]-sigmatropic rearrangements to give 2-(disilylallenyl)glycine derivatives, interesting highly functional synthons, in moderate to good yield (30 to 85%) and in high diastereoselectivity when directed by a large silylpropargyl group (9:1 to 22:1). The highly functional amino acid, methyl (R)-2-(Boc-amino)-3,5-bis(trimethylsilyl)hexa-3,4-dienoate was isolated and characterized by X-ray crystal structure analysis.

publication date

  • 2009