475115-18-5Relevant academic research and scientific papers
A highly efficient and practical new allylboronate tartramide for the asymmetric allylboration of achiral aldehydes
Chen, Wansuo,Liu, Yanzhu,Chen, Zhirong
, p. 1665 - 1668 (2005)
Chiral homoallylic alcohols can be prepared from aldehydes upon reaction with two optically pure allylboronate tartramides. The enantiomeric excess is 10-15% higher for the allylation of benzaldehyde when using N,N'-dibenzyl-tartramide auxiliary 5b than when using N,N'-diphenyl-tartramide (5a). 2-Allyl-N,N'-dibenzyl-1,3,2-dioxaborolane-4,5-dicarbamide (2b) affords homoallylic alcohols with 90-99% ee upon reaction with some representative aldehydes. The derivatised chiral auxiliaries can be recovered by simple recrystallization, in 85% yield, without any loss of specific rotation. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
