73130-83-3Relevant academic research and scientific papers
Preparation of 3,3-bis(tributylstannyl)propenes, potential new 1,3-allyl dianions
Madec, David,Ferezou, Jean-Pierre
, p. 6657 - 6660 (1997)
(E)-1-(tert-Butyldimethyl)silyloxy-3,3-bis(tributylstannyl)propene 11 as well as 1-N,N-diisopropylcarbamoyloxy-3,3-bis(tributylstannyl)propene 10 have been prepared upon addition of Bu3Sn(Bu)Cu(CN)Li2 8 to diverse γ-heterosubstituted acrolein precursors, followed by addition of excess HMPA and of the required electrophile. A E/Z ratio of 95:5 was reached in the case of 11. The reaction may occur through an addition-elimination-addition sequence where the stannylated acrolein B is thought to be a common intermediate. The best results were obtained upon single conjugate addition of 8 to (E)-3-(tributylstannyl)-2-propenal 12 (78%). A two-pot synthesis of the title compound was developed from the inexpensive malonaldehyde bis(dimethyl)acetal 14.
Water-Promoted Organic Synthesis using Glyco-Organic Substrates: the Claisen Rearrangement
Lubineau, Andre,Auge, Jacques,Bellanger, Nathalie,Caillebourdin, Sylvie
, p. 1631 - 1636 (2007/10/02)
The preparation of new glyco-organic substrates, along with their enhanced reactivity in water-promoted Claisen rearrangement, are described.The chirality induced by the glucose moiety during the course of the reaction is dependent upon the α- or β-configuration of the anomeric centre.This allowed us to prepare enantiomerically pure (R) or (S) 1,3-diols 8, with D-glucose, as the unique source of chirality.
