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.Electric Literature of C10H9NO2.Zhang, Jian; Gao, Yan-Shan; Gu, Bu-Ming; Yang, Wu-Lin; Tian, Bo-Xue; Deng, Wei-Ping published the article 《Cooperative N-heterocyclic Carbene and Iridium Catalysis Enables Stereoselective and Regiodivergent [3 + 2] and [3 + 3] Annulation Reactions》 about this compound( cas:21778-81-4 ) in ACS Catalysis. Keywords: pyrroloindole preparation enantioselective diastereoselective regioselective; indolyl allyl carbonate enal cyclization carbene iridium catalyst; formylcyclopropane enal cyclization carbene iridium catalyst; pyridineindole preparation enantioselective diastereoselective regioselective; enal indolyl allyl carbonate cyclization carbene iridium catalyst. Let’s learn more about this compound (cas:21778-81-4).
A cooperative N-heterocyclic carbene (NHC)/iridium catalysis has been developed to achieve highly stereoselective and regiodivergent [3 + 2] and [3 + 3] annulation reactions of 2-indolyl allyl carbonates I (R = H, Me; R1 = H, OMe, Me, F, Cl; R1 = H, OMe, Cl) with enals R3CH=CHCHO (R1 = Ph, hexyl, 4-chlorophenyl, furan-2-yl, etc.). The use of the NHC catalyst has introduced switchable homoenolate and enolate intermediates from the common enal precursor via a simple adjustment of reaction conditions in a predictable manner. This protocol furnishes two types of biol. important products, pyrrolo[1,2-a]indoles II and pyridine[1,2-a]indoles III, with high diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Notably, all four stereoisomers of these products with two vicinal stereocenters could be afforded through permutations of the enantiomers of the two chiral catalysts. Mechanistic investigations and further computational d. functional theory calculations give an explanation of the origin of the regioselectivity. In addition, the NHC-enolate intermediate generated from formylcyclopropanes IV (R4 = Ph, tert-Bu, naphthalen-2-yl, etc.) was also compatible in this cooperative catalytic system and thus the arsenal of optically pure pyrrolo[1,2-a]indole products V was enriched.
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Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem