1178609-32-9Relevant articles and documents
A diastereoselective one-pot, three-step cascade toward α-substituted allylboronic esters
B?se, Dietrich,Niesobski, Patrik,Lübcke, Marvin,Pietruszka, J?rg
, p. 4699 - 4703 (2014/06/09)
A new highly diastereoselective synthesis of chiral α-substituted allylboronic esters, based on a one-pot, three-step cascade, is presented. The palladium- and acid-cocatalyzed reaction cascade involves a desilylation of a TBS-protected allylic alcohol, borylation, and addition of an allyl group to an aldehyde. Herein we present the first application of a TBS-protected allylic alcohol in a palladium-catalyzed borylation/allylation reaction.
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.
Palladium-catalyzed carbonyl allylation: Synthesis of enantiomerically pure α-substituted allylboronic esters
Fernández, Enrique,Pietruszka, J?rg
experimental part, p. 1474 - 1476 (2009/10/23)
Palladium-catalyzed carbonyl allylation of stable alkenylboronic ester with SnCl2 proceeded diastereoselectively to afford a-substituted allylboronic esters; the assignment of their configuration as well as allyl additions are presented. Georg