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.