Intramolecular hetero-Diels-Alder reaction of prolinal-derived N-arylimines : Lewis acid-dependent reversal of the diastereoselectivity

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1994

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Intramolecular Lewis acid-catalyzed hetero-Diels-Alder reaction of L-prolinal-derived N-arylimine 1 yielded diastereoselectively either the cis,cis-azacyclopenta[a]anthracene derivative 2a or the trans,trans-isomer 2b, depending on the Lewis acid.

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