Enantioselective organocatalyzed functionalization of benzothiophene and thiophenecarbaldehyde derivatives

• Published in: Tetrahedron Vol. 68; no. 24; pp. 4773 - 4781
• Main Authors: Secci, Francesco, Cadoni, Enzo, Fattuoni, Claudia, Frongia, Angelo, Bruno, Giuseppe, Nicolò, Francesco
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.06.2012; Elsevier
• Subjects: Adducts; Aldehydes; Aldol reactions; Benzothiophene; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Derivatives; Enantioselectivity; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Inversions; Ketones; Organic chemistry; Organocatalysis; Physical Sciences; Preparations and properties; Regiochemistry; Science & Technology; Tetrahedrons; Tetrazoles; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Benzothiophene; Enantioselectivity; Regiochemistry; Organocatalysis; Aldol reactions; REACTIVITY; ALDEHYDES; TRANSITION-STATES; IDENTIFICATION; THIOPHENE; HYDROXYACETONE; REPLICATION; LIGANDS; ASYMMETRIC ALDOL REACTIONS; INHIBITORS; Tetrazole derivatives; Catalytic reaction; Nitrogen heterocycle; Organocatalyst; Aldehyde; Ketone; Pyrrolidine derivatives; Aldol condensation; Aldol; Benzothiophene derivatives; Thiophene derivatives; Sulfur heterocycle; Functionalization; Cross reaction; Enantiomeric excess; Catalysis; Room temperature
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.04.008

Herein we report a study on the enantioselective organocatalyzed cross-aldol reaction of 1-benzothiophene and thiophenecarbaldehydes with different ketones. The reactions were conducted at 0°C or room temperature to afford the corresponding adducts in high yields and good to excellent ee using different organocatalysts. Interestingly, using (S)-pyrrolidine tetrazole and acetoxyacetone an inversion of the aldol regiochemistry was observed. [Display omitted]