title: Synthesis of polyhydroxylated pyrrolidines from sugar-derived bromonitriles through a cascade addition of allylmagnesium bromide/cyclization/reduction.
abstract: The synthesis of polyhydroxylated 2-allylpyrrolidines from sugar-derived bromonitriles in a cascade addition of allylmagnesium bromide/SN2 cyclization/reduction with Zn(BH4)2 is described. The stereochemical course of the reduction step is rationalized. Two of the obtained compounds are transformed into stereoisomers of naturally-occurring iminosugar (+)-lentiginosine. In an alternative approach, 2,2-diallylpyrrolidines are obtained from bromonitriles in a cascade addition of allylmagnesium bromide/SN2 cyclization/addition of another equivalent of allylmagnesium bromide.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. sljar@icho.edu.pl mmalik@icho.edu.pl.
authors.forename: Michał
authors.initials: M
authors.lastname: Malik
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. sljar@icho.edu.pl mmalik@icho.edu.pl.
authors.forename: Sławomir
authors.initials: S
authors.lastname: Jarosz
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D003500:Cyclization; D017616:Magnesium Compounds / Q000737:chemistry; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D001965:Bromides; D002241:Carbohydrates; D017616:Magnesium Compounds; D009570:Nitriles; D009942:Organometallic Compounds; D011759:Pyrrolidines; C586611:magnesium bromide