title: Frequency of C-allylations on oligoglycinates via N-ylides.
abstract: The highly selective mono-C-allylation of oligoglycinates such as a diethylenetriaminepentaacetate, an iminodiacetate, and an ethylenediaminetetraacetate via insertion of a vacuum operation between the N-allylation and C-migration steps is reported. It is contrastive that one-pot N-allylation-C-allylation procedure gave a mixture including multiallylated products. In the reaction with N-ylides, gem-C-diallylation and α,α'-C-diallylation of oligoglycinates are strongly inhibited even with the use of an excess of allyl bromide and base. A mechanism to explain this control of the frequency of C-allylation on oligoglycinates via N-ylides is also proposed.
authors.affiliation: Department of Pharmaceutical Chemistry, Institute of Health Biosciences, Graduate School of The University of Tokushima, 1-78-1 Sho-machi, Tokushima 770-8505, Japan. nem@ph.tokushima-u.ac.jp
authors.forename: Hisao
authors.initials: H
authors.lastname: Nemoto
authors.forename: Shin-ya
authors.initials: SY
authors.lastname: Tamagawa
authors.forename: Kenji
authors.initials: K
authors.lastname: Yatsuzuka
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Kawamura
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005998:Glycine / Q000737:chemistry*; D007098:Imino Acids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000085:Acetates; D000498:Allyl Compounds; D007098:Imino Acids; D002244:Carbon; D005998:Glycine