Chan, Yuk-Cheung; Sak, Marcus H.; Frank, Scott A.; Miller, Scott J. published the article 《Tunable and Cooperative Catalysis for Enantioselective Pictet-Spengler Reaction with Varied Nitrogen-Containing Heterocyclic Carboxaldehydes》. Keywords: heterocyclic tetrahydro carboline preparation enantioselective; benzylindolyl ethanamine carboxaldehyde Pictet Spengler squaramide carboxylic acid catalyst; Pictet-Spengler; cooperative catalysis; heterocycles; hydrogen bond donors; peptides.They researched the compound: 5-Chloropicolinaldehyde( cas:31181-89-2 ).Application In Synthesis of 5-Chloropicolinaldehyde. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:31181-89-2) here.
Herein an organocatalytic enantioselective functionalization of heterocyclic carboxaldehydes RCHO (R = Ph, pyridin-3-yl, 1H-imidazol-2-yl, etc.) via the Pictet-Spengler reaction was reported. Through careful pairing of novel squaramide and Bronsted acid catalysts, this method tolerates a breadth of heterocycles, enabling preparation of a series of heterocycle conjugated β-(tetrahydro)carbolines I (R1 = Bn, 3-ethoxy-3-oxopropyl, 2-methoxy-2-oxoethyl, etc.) in good yield and enantioselectivity. Careful selection of carboxylic acid co-catalyst is essential for toleration of a variety of regioisomeric heterocycles I. Utility is demonstrated via the three-step stereoselective preparation of pyridine-containing analogs I (R = 5-chloropyridin-2-yl; R1 = 3-ethoxy-3-oxopropyl, 2-methoxy-2-oxoethyl, 2-carboxyethyl, carboxymethyl) of potent selective estrogen receptor downregulator and U.S. FDA approved drug Tadalafil.
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Reference:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate