Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines
We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10–20 minutes with high enantioselectivity (89–98 % de/ee), moderate yields and a wide functional group tolerance.
Poh, Jian-Siang,Makai, Szabolcs,von Keutz, Timo,Tran, Duc N.,Battilocchio, Claudio,Pasau, Patrick,Ley, Steven V.
supporting information
p. 1864 - 1868
(2017/02/05)
An efficient and general one-pot method for the synthesis of chiral bis(oxazoline) and pyridine bis(oxazoline) ligands
An expeditious method for the synthesis of chiral box and pybox ligands is reported. The approach is based on a one-pot condensation reaction of chiral β-amino alcohols with a dinitrile using stoichiometric or catalytic amounts of zinc triflate. Yields gr
Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions
The synthesis of a series of iron-pybox complexes and their employment in the catalytic asymmetric aziridine forming reaction is presented. When AgSbF6 is used as an initiator, the i-pr- and t-bu-pybox complexes produce 47% of the cis-aziridine
Redlich, Mark,Hossain, M. Mahmun
p. 8987 - 8990
(2007/10/03)
Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes.
The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic depen
Schaus,Jacobsen
p. 1001 - 1004
(2007/10/03)
Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines
Chiral oxazolinylpyridines bearing an oxazolinyl [bis(oxazolinyl)pyridines] or a cyano group in the 6-position of the pyridine ring were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acet