title: Diversity-oriented asymmetric catalysis (DOAC): stereochemically divergent synthesis of thiochromanes using an imidazoline-aminophenol-nickel-catalyzed Michael/Henry reaction.
abstract: The (S,S)-diphenylethylenediamine-derived imidazoline-aminophenol-Ni complex catalyzed tandem asymmetric Michael/Henry reaction of 2-mercaptobenzaldehydes with β-nitrostyrenes to give the corresponding (2S,3R,4R)-2-aryl-3-nitrothiochroman-4-ols in up to 99% diastereoselectivity with 95% ee was demonstrated in diversity-oriented asymmetric catalysis. Reduction of the nitro group of the chiral thiochromanes gave a new series of (2S,3R,4R)-3-amino-2-arylthiochroman-4-ols with retention of the strereoselectivity.
authors.affiliation: Department of Chemistry, Graduate School of Science, Chiba University , 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
authors.forename: Takayoshi
authors.initials: T
authors.lastname: Arai
authors.forename: Yushi
authors.initials: Y
authors.lastname: Yamamoto
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000627:Aminophenols / Q000737:chemistry*; D002384:Catalysis; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D048288:Imidazolines / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000627:Aminophenols; D002839:Chromans; D048288:Imidazolines; D013457:Sulfur Compounds; D009532:Nickel