Synthesis of Axially Chiral Amino Acid and Amino Alcohols via Additive−Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent Transformations of the Product Amidoaza[5]helicene

• Published in: Journal of organic chemistry Vol. 75; no. 20; pp. 7010 - 7013
• Main Authors: Furuta, Takumi, Yamamoto, Junya, Kitamura, Yuki, Hashimoto, Ayano, Masu, Hyuma, Azumaya, Isao, Kan, Toshiyuki, Kawabata, Takeo
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 15.10.2010
• Subjects: Amides - chemistry; Amino Acids - chemical synthesis; Amino Acids - chemistry; Amino Alcohols - chemical synthesis; Amino Alcohols - chemistry; Chemistry; Condensed benzenic and aromatic compounds; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Ligands; Molecular Structure; Organic chemistry; Organometallic Compounds - chemistry; Palladium - chemistry; Preparations and properties; Stereoisomerism; Catalytic reaction; Aminoalcohol; Nitrogen heterocycle; Lactam; Alcohol; Palladium complex; Chiral compound; Naphthalene derivatives; Ring cleavage; Chemical coupling; Aminoacid; Optical activity; Helicene; Aromatic compound; Chemical synthesis; Successive reaction
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo101524t

Novel optically active axially chiral amino acid and amino alcohols have been synthesized efficiently via lactam ring-opening, with the aid of an optically active alcohol, amidoaza[5]helicene 5, which has been readily prepared by an additive-ligand-free Pd catalyzed domino coupling reaction in a single step. The stereostructures of these chiral molecules have also been clarified.