Zinc-mediated allylation of aldoxime esters

Highly γ-Regioselective 1,2-Addition of α,β-Unsaturated Oxime Ethers with Allylzinc Bromides: A Straightforward Approach for the Synthesis of Homoallylic Amines

“…Consistent with the previous works reported by Wolan,24 the reaction of simple oxime ether with allylzinc reagent does not take place (Scheme 4).…”

Metal-Involving Synthesis and Reactions of Oximes

“…The aldoxime esters R 1 C 6 H 4 C(H)NOC(O)R 2 (141) reacted with the allyl bromides BrCH 2 C(H)CHR 3 (R 3 = H, Ph) in the presence of Zn in a mixture of THF and aqueous NH 4 Cl at RT for 30 min to give N-allyl hydroxylamines 142 in good to excellent yields (48−98%; Scheme 66, a). 372 The reaction did not proceed in the case of the oxime and oxime ethers PhC 373,374 The reported procedure provides 144 (75−94%; de 76−99%; except G: de 10%, and D: de 37%). This reductive allylation could also be catalyzed by Zn(OTf) 2 or AgOTf instead of Sn(OTf) 2 , but the yields were somewhat lower.…”

“…The aldoxime esters R 1 C 6 H 4 C­(H)NOC­(O)­R 2 ( 141 ) reacted with the allyl bromides BrCH 2 C­(H)CHR 3 (R 3 = H, Ph) in the presence of Zn in a mixture of THF and aqueous NH 4 Cl at RT for 30 min to give N -allyl hydroxylamines 142 in good to excellent yields (48–98%; Scheme , a) . The reaction did not proceed in the case of the oxime and oxime ethers PhC­(H)NOR (R = H, Piv, CH 2 Ph).…”

Synthesis of N‐(2,3,4,5,6‐Pentafluorobenzyloxy)‐γ‐lactams by Rhodium‐Catalyzed Cyclization of Diazo Amides

“…Utilization of N ‐alkoxy diazo amides in such cyclizations is an attractive approach because of their relatively simple preparation and potential in further transformations of N ‐alkoxy amides 34,35. Recently, N ‐alkoxy diazo amides were used by Sintim and co‐workers for intramolecular C–H insertions and cyclopropanation reactions 36,37.…”