Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 333-339
doi: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.
Keywords: homopropargylic; oxazolidinones; rearrangement; α-aminoallenylstannanes; α-aminopropargylboranes.
*Pure Appl. Chem. 78, 197-523. An issue of reviews and research papers based on lectures presented at the 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), Geneva, Switzerland, 17-21 July 2005.