343312-57-2Relevant academic research and scientific papers
Synthesis of highly oxygenated enantiomerically pure cis-bicyclo[4.3.0]nonanes from secondary sugar allyltin derivatives
Jarosz, Slawomir,Szewczyk, Katarzyna,Zawisza, Anna
, p. 1709 - 1713 (2007/10/03)
Secondary sugar allyltin derivatives of the D-series: Sug-CH(SnBu3)-CH=CH2 (obtained in an SN2′ reaction of the corresponding primary allylic mesylates with 'Bu3SnCu') with the S-configuration at the stereogenic
Stability of regioisomeric sugar allyltins. Cleavage of the carbon-oxygen bond under radical conditions
Jarosz, Slawomir,Szewczyk, Katarzyna
, p. 3021 - 3024 (2007/10/03)
Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140°C) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170°C.
