133210-27-2Relevant academic research and scientific papers
Evidence for synclinal transition state in the reactions of aromatic aldehydes with α-(alkoxy)allylstannanes
Gung, Benjamin W.,Smith, Daniel T.,Wolf, Mark A.
, p. 5455 - 5466 (2007/10/02)
Unlike aliphatic aldehydes, aromatic aldehydes produce greater than 95% of syn-(Z) enol ether when treated with α-(alkoxy)allylstannanes in the presence of BF3·Et2O. However, in the presence of TiCl4, the reaction of p-chloro-o-methoxybenzaldehyde with α-(alkoxy)crotylstannane produced predominantly the syn-(E) isomer.
Remarkable increase in the diastereofacial selectivity of the addition of β-methyl α-(alkoxy)allylstannane to aldehydes: Substituent effects on diastereofacial selectivity
Gung, Benjamin W.,Smith, Daniel T.,Wolf, Mark A.
, p. 13 - 16 (2007/10/02)
Several new chiral allylstannanes were prepared and reacted with aldehydes. Excellent diastereofacial selectivity was observed for the reactions of allylstannane 1 with aldehydes in the presence of BF3·Et2O. This is in contrast to the results from other allylstannanes which do not bear a β-methyl group. These observations were rationalized based on a combination of steric and electronic effects.
