Syntheses and reactions of optically active α-aminoallenylstannanes and α-aminopropargylboranes

Hegedus, Louis S.; Ranslow, Peter; Achmatowicz, Michal; de los Rios, Cristobal; Hyland, Christopher; Garcia-Frutos, Eva M.; Salman, Sarri

doi:10.1351/pac200678020333

Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 333-339

http://dx.doi.org/10.1351/pac200678020333

Syntheses and reactions of optically active α-aminoallenylstannanes and α-aminopropargylboranes

Louis S. Hegedus, Peter Ranslow, Michal Achmatowicz, Cristobal de los Rios, Christopher Hyland, Eva M. Garcia-Frutos and Sarri Salman

Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA

Abstract: An efficient synthesis of α-aminoallenylstannane from propargyloxazolidinone has been developed. It undergoes reaction with aldehydes to give homopropargylic alcohols with high syn selectivity. Epoxides undergo a similar reaction preceded by rearrangement to the aldehyde. These alcohols were used in the synthesis of β-amino acids, azasugars, and deoxyaminohexoses. Imines underwent reaction with this stannane to give 1,2-diamines. The related propargylborane reacts with aldehydes to produce allenyl carbinols. The Co₂(CO)₆ complexes of propargyloxazolidinones were developed as an α-aminopropargyl cation equivalent.