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Syntheses and reactions of optically active alpha-aminoallenyistannanes and alpha-aminopropargylboranes


Hegedus, LS and Ranslow, P and Achmatowicz, M and Rios, C and Hyland, CJT and Garcia-Frutos, EM and Salman, S, Syntheses and reactions of optically active alpha-aminoallenyistannanes and alpha-aminopropargylboranes, Pure and Applied Chemistry, 78, (2) pp. 333-339. ISSN 0033-4545 (2006) [Refereed Article]

DOI: doi:10.1351/pac200678020333


An efficient synthesis of alpha-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 beta-amino acids, azasugars, and deoxyammohexoses. 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 alpha-aminopropargyl cation equivalent.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Hyland, CJT (Dr Chris Hyland)
ID Code:72653
Year Published:2006
Web of Science® Times Cited:6
Deposited By:Chemistry
Deposited On:2011-08-30
Last Modified:2011-10-25

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