eCite Digital Repository
Syntheses and reactions of optically active alpha-aminoallenyistannanes and alpha-aminopropargylboranes
Citation
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
Abstract
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 |
| Downloads: | 0 |
Repository Staff Only: item control page