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

Conference Paper


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 Co 2(CO)6 complexes of propargyloxazolidinones were developed as an α-aminopropargyl cation equivalent. © 2006 IUPAC.

Publication Date


  • 2006

Citation


  • Hegedus, L. S., Ranslow, P., Achmatowicz, M., De Los Rios, C., Hyland, C., Garcia-Frutos, E. M., & Salman, S. (2006). Syntheses and reactions of optically active ¿-aminoallenylstannanes and ¿-aminopropargylboranes. In Pure and Applied Chemistry Vol. 78 (pp. 333-339). doi:10.1351/pac200678020333

Scopus Eid


  • 2-s2.0-33644545992

Start Page


  • 333

End Page


  • 339

Volume


  • 78

Issue


  • 2

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 Co 2(CO)6 complexes of propargyloxazolidinones were developed as an α-aminopropargyl cation equivalent. © 2006 IUPAC.

Publication Date


  • 2006

Citation


  • Hegedus, L. S., Ranslow, P., Achmatowicz, M., De Los Rios, C., Hyland, C., Garcia-Frutos, E. M., & Salman, S. (2006). Syntheses and reactions of optically active ¿-aminoallenylstannanes and ¿-aminopropargylboranes. In Pure and Applied Chemistry Vol. 78 (pp. 333-339). doi:10.1351/pac200678020333

Scopus Eid


  • 2-s2.0-33644545992

Start Page


  • 333

End Page


  • 339

Volume


  • 78

Issue


  • 2