162813-15-2Relevant academic research and scientific papers
CHELATION CONTROLLED ALLYLATION OF ALDEHYDES WITH A CHIRAL ALLYLSILYLENE DERIVED FROM (-)-10-PHENYLPINANEDIOL
Shanmuganathan, Kirupathevy,French, Larry G.,Jensen, Bruce L.
, p. 797 - 800 (1994)
The chiral allylsilylene prepared from (-)-10-phenylpinanediol reacts with chiral α-alkoxy aldehydes in the presence of stannic chloride to afford homoallylic alcohols with diastereofacial selectivity ratios as high as 100:0.The results are consistent with attack of the allylsilylene on the less hindered face of the chelated intermediate.Our preliminary studies on several silylenes prepared from bicyclo systems revealed that substituent effects on the chiral auxiliary and the silicon atom play an important role in the selectivity of these unique compounds.
