title: Synthesis of octitols and the respective amino-derivatives from 'organo-aldols'.
abstract: Two diastereoisomeric keto-octoses, obtained in the reaction of 2,3:4,5-diacetone-D-arabinose with protected dihydroxyacetone catalyzed with L- or D-proline, were converted into octitols by stereoselective reduction of the carbonyl group with zinc borohydride and final deprotection. The study on the preparation of the respective amino-derivatives by reductive amination of these organo-adducts is presented; stereochemical aspects of these processes are discussed.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Łęczycka
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland.
authors.forename: Bartosz
authors.initials: B
authors.lastname: Chaciak
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland.
authors.forename: Maciej
authors.initials: M
authors.lastname: Cieplak
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka, 44, 01-224 Warszawa, Poland. Electronic address: slawomir.jarosz@icho.edu.pl.
authors.forename: Sławomir
authors.initials: S
authors.lastname: Jarosz
mesh_terms: D000096:Acetone / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002241:Carbohydrates; D000096:Acetone
keywords: Amino-octitols; Octitols; Organocatalysis; Stereoselective synthesis