1001652-60-3Relevant academic research and scientific papers
Palladium-catalyzed synthesis of enantiomerically pure α-substituted allylboronic esters and their addition to aldehydes
Fernandez, Enrique,Pietruszka, Joerg,Frey, Wolfgang
supporting information; experimental part, p. 5580 - 5589 (2010/11/17)
Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl2 to obtain enantiomerically pure α-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple diastereoselectivity to form anti-products. Their addition to aldehydes yields enantiomerically enriched homoallylic alcohols 17 and 18, respectively. Synthesis, characterization, and a mechanistic rational is presented here.
Concerning the selective protection of (Z)-1,5-syn-ene-diols and (E)-1,5-anfi-ene-diols as allylic triethylsilyl ethers
Hicks, Jacqueline D.,Huh, Chan Woo,Legg, Ashley D.,Roush, William R.
, p. 5621 - 5624 (2008/09/18)
Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 °C effects selective silylation of the allylic alcohol with >95:5 chemoselectivity when the allylic and homoallylic
Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence
Flamme, Eric M.,Roush, William R.
, p. 13644 - 13645 (2007/10/03)
Highly diastereo- and enantioselective syntheses of 1,5-disubstituted (E)-1,5-anti-pent-2-endiols 1 and (Z)-1,5-syn-pent-2-endiols 2 have been achieved via the one-pot coupling of two different aldehydes with either (E)-γ-(1,3,2-dioxaborinanyl)-allyl]diis
