title: Diversity through isosterism: the case of boron-substituted 1,2-dihydro-1,2-azaborines.
abstract: The first general synthesis of boron-substituted 1,2-dihydro-1,2-azaborines is described. The versatile 1,2-dihydro-1,2-azaborine precursor 4 is synthesized through a ring-closing metathesis-oxidation sequence. Treatment of 4 with a wide range of anionic nucleophiles furnishes the desired adducts 5 in good yields. The scope includes hydrogen- and a variety of carbon- and heteroatom-based nucleophiles. Furthermore, the boron-containing isostere (7) of the potent hypolipidemic agent, methyl 2-ethylphenoxyacetate (8), is readily prepared through our method.
authors.affiliation: Department of Chemistry, University of Oregon, Eugene, OR 97403, USA.
authors.forename: Adam J V
authors.initials: AJ
authors.lastname: Marwitz
authors.forename: Eric R
authors.initials: ER
authors.lastname: Abbey
authors.forename: Jesse T
authors.initials: JT
authors.lastname: Jenkins
authors.forename: Lev N
authors.initials: LN
authors.lastname: Zakharov
authors.forename: Shih-Yuan
authors.initials: SY
authors.lastname: Liu
mesh_terms: D000147:Acids, Heterocyclic / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001895:Boron / Q000737:chemistry*; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D000147:Acids, Heterocyclic; D001372:Aza Compounds; D001896:Boron Compounds; D006859:Hydrogen; D001895:Boron