The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ) is researched.Product Details of 21778-81-4.Bandini, Marco; Melloni, Alfonso; Piccinelli, Fabio; Sinisi, Riccardo; Tommasi, Simona; Umani-Ronchi, Achille published the article 《Highly Enantioselective Synthesis of Tetrahydro-β-Carbolines and Tetrahydro-γ-Carbolines Via Pd-Catalyzed Intramolecular Allylic Alkylation》 about this compound( cas:21778-81-4 ) in Journal of the American Chemical Society. Keywords: beta gamma carboline enantioselective regioselective preparation; pyrrolopyridine enantioselective regioselective preparation; indolylmethylamino butenol carbonate preparation enantioselective regioselective cyclocondensation; palladium catalyzed asym intramol allylic alkylation indolylmethylamino butenol carbonate; mol crystal structure beta carboline camphorsulfonamide. Let’s learn more about this compound (cas:21778-81-4).
(2-Indolylmethylamino) or (3-indolylmethylamino)butadienyl carbonates such as I and a (pyrrolylmethylamino)butadienyl carbonate undergo enantioselective intramol. allylic alkylation reactions in the presence of tris(dibenzylideneacetone)palladium and nonracemic (diphenylphosphinobenzoyl)diamines such as II to yield nonracemic tetrahydro-β-carbolines, tetrahydro-γ-carbolines, and a pyrrolopyridine such as III (R = PhCH2) and IV (R = PhCH2) in 82-97% ee. (indolylmethylamino)butadienyl or (pyrrolylmethylamino)butadienyl carbonates such as I are prepared from indolecarboxaldehydes by imine formation and reduction, alkylation of the amines with bromobutenoate esters (or a bromobutenal), reduction of the ester or aldehyde with diisobutylaluminum hydride, and acylation with Me chlorocarbonate. A variety of ligands for the cyclocondensation are tried; diphenylphosphinobenzamides such as II give carbolines with the highest regioselectivities and enantioselectivities of the ligands tried. (indolylmethylamino)butadienyl carbonates substituted either on the indole or the butenyl moieties yield carbolines with similar enantio- and regioselectivities. An (E)-3-indolylmethylaminobutenol carbonate undergoes regio- and enantioselective allylic alkylation to yield a γ-carboline in 90% yield and 93% yield, while intramol. allylic alkylation of the corresponding (Z)-3-indolylmethylaminobutenol carbonate yields the opposite enantiomer in 65% yield and in 5% ee. The absolute configuration of III (R = PhCH2) is determined by X-ray crystallog. anal. of a β-carboline (-)-camphorsulfonamide derived from its enantiomer [the minor stereoisomer generated in the allylic alkylation which yields III (R = PhCH2)].
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