Diversity through isosterism: the case of boron-substituted 1,2-dihydro-1,2-azaborines.
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.
Marwitz
Adam J V
AJ
Department of Chemistry, University of Oregon, Eugene, OR 97403, USA.
Abbey
Eric R
ER
Jenkins
Jesse T
JT
Zakharov
Lev N
LN
Liu
Shih-Yuan
SY
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
D000147:Acids, Heterocyclic; D001372:Aza Compounds; D001896:Boron Compounds; D006859:Hydrogen; D001895:Boron