Efficient Routes to a Diverse Array of Amino Alcohol-Derived Chiral Fragments

• Published in: ACS combinatorial science Vol. 18; no. 9; pp. 569 - 574
• Main Authors: Haftchenary, Sina, Nelson, Shawn D, Furst, Laura, Dandapani, Sivaraman, Ferrara, Steven J, Bošković, Žarko V, Figueroa Lazú, Samuel, Guerrero, Adrian M, Serrano, Juan C, Crews, DeMarcus K, Brackeen, Cristina, Mowat, Jeffrey, Brumby, Thomas, Bauser, Marcus, Schreiber, Stuart L, Phillips, Andrew J
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.09.2016; Amer Chemical Soc
• Subjects: Amino Alcohols - analysis; Amino Alcohols - chemistry; Chemistry; Chemistry, Applied; Chemistry, Medicinal; Chemistry, Multidisciplinary; Drug Discovery; Humans; Lactams - chemistry; Life Sciences & Biomedicine; Molecular Weight; Morpholines - chemistry; Naphthalenesulfonates - chemistry; Oxazolidinones - chemistry; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Stereoisomerism; chiral fragments; drug discovery; amino alcohols; fragment-based lead discovery; 2-OXAZOLIDINONES; BAYLIS-HILLMAN REACTIONS; ASYMMETRIC-SYNTHESIS; TERMINAL EPOXIDES; LEAD DISCOVERY; ENANTIOSELECTIVE SYNTHESIS; ANTITUMOR-ACTIVITY; SUBSTITUTED MORPHOLINES; KINETIC RESOLUTION
• ISSN: 2156-8952; 2156-8944; 2156-8944
• DOI: 10.1021/acscombsci.6b00050

Efficient syntheses of chiral fragments derived from chiral amino alcohols are described. Several unique scaffolds were readily accessed in 1–5 synthetic steps leading to 45 chiral fragments, including oxazolidinones, morpholinones, lactams, and sultams. These fragments have molecular weights ranging from 100 to 255 Da and are soluble in water (0.085 to >15 mM).