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.
Conference
IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 13th, Geneva, Switzerland, 2005-07-17–2005-07-21
© 2013 Walter de Gruyter GmbH, Berlin/Boston
