Collect. Czech. Chem. Commun. 2009, 74, 927-934
Published online 2009-06-01 11:40:12

α-(Disilylallenyl) α-amino acid derivatives from the Claisen rearrangement of propargyl glycinates

Mustafa Mohamed and Michael A. Brook*

Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, L8S 4M1, Canada


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.

Keywords: Allenes; [3,3]-Sigmatropic rearrangements; Claisen rearrangement; Amino acids; Propargyl esters.

References: 17 live references.