“…Although F−C alkylation reactions that utilize metal salts with catalytic amounts of an optically active ligand have been developed recently, , to the best of our knowledge, no precedent has materialized on an asymmetric 1,2-aza-F−C reaction of aldimines promoted by organocatalysts − we focused on the development of an enantioselective 1,2-aza-F−C reaction of a furan with N -Boc aldimine derivatives (eq 1). …”
A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral gamma-butenolid.
“…Although F−C alkylation reactions that utilize metal salts with catalytic amounts of an optically active ligand have been developed recently, , to the best of our knowledge, no precedent has materialized on an asymmetric 1,2-aza-F−C reaction of aldimines promoted by organocatalysts − we focused on the development of an enantioselective 1,2-aza-F−C reaction of a furan with N -Boc aldimine derivatives (eq 1). …”
A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral gamma-butenolid.
“…6 The absolute stereochemistry being (2R,3S,4S) was established on the basis of chemical correlation studies. 7 As a result, many approaches have been developed for the asymmetric synthesis of anisomycin (1) [8][9][10][11][12][13][14][15] but there is still a need for more efficient and elegant procedure In the continuation of our efforts on the application of a methodology with the use of α-amino aldehydes to the synthesis of thyrosinal (D-4) in the addition reaction should give desired syn-adduct predominantly. Among several possible N-protecting groups, the Boc group was selected since it can be easily removed under mild conditions.…”
Anisomycin analogue precursor was synthesised starting from a suitably protected α-amino aldehyde -tyrosine. The crucial step involves the addition of acetylenic reagent to N-Boc-Omethyl-L-tyrosinal in the presence of zinc(II) bromide, affording a syn-acetylenic adduct with high diastereoselectivity.
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