54620-75-6Relevant academic research and scientific papers
Concentration effects in chelation controlled reactions
Springer,Springer, James B.,DeBoard,Deboard, Julie,Corcoran,Corcoran, Robert C.
, p. 8733 - 8736 (2007/10/02)
The diastereoselectivities of addition reactions of allyltrimethylsilane to an α-benzyloxyaldehyde were found to be relatively insensitive to the amount of added TiCl4, and to the absolute concentration of the 1:1 aldehyde/TiCl4 complex. In contrast, diastereoselectivities of similar additions to a structurally related β-benzyloxyaldehyde were highly dependent on these variables.
Asymmetric Hetero-Diels-Alder Reaction of α-Alkoxy Aldehydes with Activated Dienes. The Scope of Lewis Acid Chelation-Controlled Cycloadditions
Midland, M. Mark,Koops, Roger W.
, p. 5058 - 5065 (2007/10/02)
The cycloaddition reactions of various α-alkoxy aldehydes with 1,3-dimethoxy-1--1,3-butadiene (Brassard's diene, 2) were performed under the Lewis acid catalysis of Eu(hfc)3, magnesium dibromide, or diethylaluminum chloride.Moderate to high diastereoselectivities were observed with Eu(hfc)3 and magnesium dibromide.Evidence from reactions of Eu(hfc)3 and magnesium dibromide catalysis indicated a possible "chelation-control" pathway.Lewis acid catalysis from diethylaluminum chloride provides products with moderate to high diastereoselectivity.The mechanistic pathway with catalysis by diethylaluminum chloride was less clear.A possible mechanism based upon a "Cram" addition is considered.
A Convenient Method for the Transformation of Allylstannanes to Alcohols, Ethers, Esters, and Amines
Takeda, Takeshi,Inoue, Tomoya,Fujiwara, Tooru
, p. 985 - 988 (2007/10/02)
Allylstannanes were easily oxidized with copper(II) bromide in the presence of water, alcohols, and sodium acetate to give the corresponding allylic alcohols, ethers, and acetates, respectively.The allylic amines were also obtained by the succesive treatm
