Lewis acid-catalyzed asymmetric radical additions of trialkyl-boranes to (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl-2H-azirine-3-carboxylate

• The asymmetric addition of alkyl radicals to (IR,2S,5R)-2-(l-methyl-l-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.

Nyckelord

azirines

asymmetric radical additions

chiral auxiliaries

glyoxylic oxime ether

alpha-amino-acids

acyclic stereocontrol

chiral aziridines

facile reaction

alkyl radicals

imines

organoboranes

2h-azirines

efficient

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art (ämneskategori)