Utilization of IndPHOX-ligands in palladium-catalysed asymmetric allylic aminations

Proofreading Experimentally Assigned Stereochemistry Through Q2MM Predictions in Pd-Catalyzed Allylic Aminations

“…Experimentally, L1 and L4 give very different selectivities of 52 % ee and 94 % ee, respectively. 44 Sterically, the ligands are very similar, and thus the force eld predicts that these two ligands should give similar selectivity results with L1 giving 93.5 % ee and L4 giving 95.3 % ee. Similar results are obtained for the related ligands L2 and L3, where the selectivities are predicted to be too high.…”

“…A validation dataset containing 77 structures (Figs. S3 and S4, Table S3 in Supporting Information) assembled from the literature 18,20,[37][38][39][40][41][42][43][44] was used to test the performance of the TSFF for systems different than the training set (Figure 2A). 1,3-Diphenyl propenyl was used as the allyl component reacting with 16 different amines, catalyzed by the Pd-complexes of 53 different P,N ligands.…”

N1‐Functionalized Indole‐Phosphane Oxazoline (IndPHOX) Ligands in Asymmetric Allylic Substitution Reactions

“…[2] 3-Oxazolylindole 4, readily prepared from indole (3), [2a] was first deprotonated with NaH and then treated with alkyl, benzyl, or carbamic halides to afford N-substituted indolyloxazolines 5a-5d. Compound 5e was synthesized by a Cucatalyzed cross-coupling reaction with phenyl bromide.…”

Palladium‐Catalyzed Enantioselective Allylic Substitution in the Presence of Monodentate Furanoside Phosphoramidites

“…88 % ee ${[\alpha ]_{\rm{D}}^{20} }$ =−26.5 ( c =0.7, CHCl 3 ), lit 24. ${[\alpha ]_{\rm{D}}^{23} }$ =+28.2 ( c =0.82, CHCl 3 ), 94 % ee ( S ), [ lit 25.…”