A silver triflimide catalyzed one-pot protocol for the diastereoselective synthesis of dihydrobenzoxepines has been {developed|created}. Silver triflimide {found|discovered|identified|located} {to be|to become} an {efficient|effective} catalyst for the formal (5+2)-cycloaddition to access dihydrobenzoxepines as a single diastereomer {using|utilizing|making use of|employing|working with|applying} vinyl diazo compounds as 5-C-synthons and ketones. An unmet challenge of {utilizing|using} the donor-/acceptor-type vinyl diazosuccinimides as 5-C-synthons {under|below|beneath} silver-catalysis is presented. This protocol {found|discovered|identified|located} {to be|to become} {highly|extremely|very|hugely} regio-, chemo- and diastereoselective, and {works|functions|operates|performs} {well|nicely|effectively|properly} with aliphatic {as well|also|too|at the same time} as aromatic methyl ketones bearing electron deactivating {as well|also|too|at the same time} as donating groups to afford dihydrobenzo[5,6]oxepino[2,3-c]pyrroles {with a|having a|using a} broad substrates scope. The {control|manage|handle} experiments and time dependent NMR {studies|research} revealed the plausible mechanism of this transformation. The protocol also proved {to be|to become} scalable {on the|around the} gram scale synthesis. 620960-38-5 Chemscene 1511297-53-2 In stock PMID:23399686
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