Diversity through isosterism: the case of boron-substituted 1,2-dihydro-1,2-azaborines |
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Authors: | Marwitz Adam J V Abbey Eric R Jenkins Jesse T Zakharov Lev N Liu Shih-Yuan |
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Institution: | Department of Chemistry, University of Oregon, Eugene, OR 97403, USA. |
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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. |
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