( S )‐(–)‐2‐Allylcyclohexanone

Abstract

Tris(dibenzylideneacetone)‐dipaldium(0)‐chloroform adduct ( S) ‐(‐)‐5,5'‐Dichloro‐6,6'‐dimethoxy‐2,2’‐bis(diphenylphosphine)‐1,1'‐biphenyl Lithium chloride Allyl methyl carrbonate Diisopropylamine n‐ Butyllithium Cyclohexanone ( S) ‐(‐)‐2‐Allylcyclohexanone

Evidence for a Non‐Concerted, Dissoziative Mechanism of the Palladium‐Catalyzed “Enolate Claisen Rearrangement” of Allylic Esters

“…Indeed, the palladium‐mediated rearrangement of the lithium enolate 5 does not occur in the absence of lithium chloride at –78 °C but requires enhancement of the temperature to 0 °C conditions that lead to an almost complete loss of enantioselectivity. These results are in accordance with the crucial role, lithium chloride was found to play in the enantioselective palladium‐catalyzed allylic alkylation of ketone enolates 20,21…”

Diastereocontrolled Formal Syntheses of (±)-Lepadiformines A, B, and C and the Divergent Synthesis of 2-epi-Lepadiformine C through Unexpected Double Consecutive Epimerizations

“…Our synthesis started from readily available quaternary α-aminonitriles 2 and 2′ , which were synthesized by the Strecker reaction of 2-allylcyclohexanone or 2-propargylcyclohexanone with cyanide in ammonia (Scheme ). The unstable free α-aminonitriles were immediately protected with CbzCl to yield 2 and 2′ in good yields.…”

The Allylic Alkylation of Ketone Enolates

“…For the allylation with a symmetrical carbonate, ( R )‐BINAP ( L4 ) as a ligand delivered the highest enantio‐ and diastereoselectivities (Scheme 13). The procedure for this reaction was furthermore published in Organic Syntheses , which underlines its reproducibility and versatility [23b,c] …”