Enantioselective allenylic alkylation reactions of unstabilized enolates have {never|by no means|in no way|never ever|under no circumstances} been reported. We now present a unified fragment-coupling {strategy|technique|method|approach|tactic} for {the first|the very first|the initial} enantioselective synthesis of α-allenylic amides and ketones {through|via|by means of|by way of} allenyl-ic alkylation of vinyl azides. In these chemodivergent reactions, cooperatively catalyzed by Ir(I)/(phosphoramidite,olefin) {complex|complicated} and Sc(OTf){3|three}, vinyl azides act {as the|because the} surrogate for {both|each} amide enolates and ketone enolates. The desiccant (molecular sieves) plays a {crucial|essential|vital|critical|important} {role|function|part} in controlling the chemodivergency of this enantioconvergent and regioselective reaction: {Under|Below|Beneath} otherwise identical reaction {conditions|circumstances|situations}, the presence {of the|from the|in the|on the|with the|of your} desiccant led to α-allenylic amides {while|whilst|although|even though|when|though} its absence resulted in α-allenylic ketones {from the|in the} {same|exact same|identical|very same|similar} substrate combinations. {Utilizing|Using} race-mic allenylic alcohols {as the|because the} alkylating agent, the {overall|general|all round} {process|procedure|method|approach|course of action} represents a dynamic kinetic asymmetric transformation (DyKAT), {where|exactly where} {both|each} α-allenylic amides and ketones are formed {with the|using the|with all the|together with the} {same|exact same|identical|very same|similar} absolute configuration {generally|usually|typically|normally|commonly|frequently} with outstanding enantioselectivity. {To the|Towards the|For the} {best|very best|greatest|ideal|finest|most effective} of our {knowledge|understanding|information|expertise|know-how}, {this is|this really is|this can be|that is} {the first|the very first|the initial} {example|instance} {of the|from the|in the|on the|with the|of your} use of vinyl azide {as the|because the} ketone enolate surrogate in an enantioselective transformation. 1-(2,2,2-Trifluoroethyl)piperazine Formula 1210830-60-6 web PMID:24101108
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