Lewis acid-catalyzed asymmetric radical additions of trialkylboranes to (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl-2H-azirine-3-carboxylate |
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Authors: | Erik Risberg Peter Somfai |
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Institution: | a KTH Chemistry, Organic Chemistry, KTH, S-100 44 Stockholm, Sweden b KTH Chemistry, Inorganic Chemistry, KTH, S-100 44 Stockholm, Sweden |
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Abstract: | The asymmetric addition of alkyl radicals to (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl-2H-azirine-3-carboxylate (1) yielding the corresponding 2-alkylaziridine-2-carboxylates has been investigated. High diastereoselectivities and good yields were obtained in the addition of primary alkyl radicals to azirine 1, while secondary radicals gave a lower dr. The influence of Lewis acids was also investigated; 10 mol% of CuCl were found to increase the dr. |
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Keywords: | Azirines Asymmetric radical addition Chiral auxiliaries |
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