Woeste, Thorsten H. published the artcileBINAP versus BINAP(O) in Asymmetric Intermolecular Mizoroki-Heck Reactions: Substantial Effects on Selectivities, Related Products of esters-buliding-blocks, the publication is Chemistry – A European Journal (2011), 17(42), 11914-11918, S11914/1-S11914/25, database is CAplus and MEDLINE.
(R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) I (R = Ph2P) and its monophosphine oxide (R)-BINAPO I [R = Ph2P(:O)] were prepared and compared as ligands in the Mizoroki-Heck reactions of 2,3-dihydrofuran and cyclopentene with Ph triflate and iodobenzene in the presence of Pd(OAc)2 and Pd2(dba)3·dba [dba = (E,E)-dibenzylideneacetone]. The regio- and enantioselectivity of the phenylation of 2,3-dihydrofuran and cyclopentene changed dramatically in the presence of hemilabile BINAP(O) instead of BINAP. The phenylation of 2,3-dihydrofuran gave different regioisomers with nearly complete selectivity when BINAP and BINAPO were used; phenylation of 2,3-dihydrofuran using BINAPO gave (R)-2-phenyl-2,5-dihydrofuran with 98:2 regioselectivity in 18-92% ee, while the use of BINAP as ligand gave (R)-5-phenyl-2,3-dihydrofuran exclusively in 16-80% ee. The phenylation of cyclopentene was more regioselective when BINAPO was used as the ligand than when BINAP was used; the reaction gave product in significantly higher enantioselectivity with BINAP(O) (60% ee) than with BINAP (10% ee). The use of Pd2(dba)3·dba instead of Pd(OAc)2 as the palladium source produced enantioselectivities as high as 86% ee in the phenylation of cyclopentene.
Chemistry – A European Journal published new progress about 126613-06-7. 126613-06-7 belongs to esters-buliding-blocks, auxiliary class Chiral Diphenols, name is (R)-[1,1′-Binaphthalene]-2,2′-diyl bis(trifluoromethanesulfonate), and the molecular formula is C7H13ClNNaO5S, Related Products of esters-buliding-blocks.
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