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The imine Ph 2 CHN CHCO 2 Et, generated from benzhydrylamine and ethyl glyoxylate, is an excellent dienophile in aza-Diels-Alder reactions, giving diastereomerically pure cycloadducts in high yield.
The imine Ph 2 CHN CHCO 2 Et, generated from benzhydrylamine and ethyl glyoxylate, provides a Diels-Alder adduct with 1,3-pentadiene from which a range of cis-2,6-disubstituted piperidines can be accessed; the benzhydryl group confers high diastereocontrol for derivatising the six-membered ring, allowing access to 2,5,6-trisubstituted piperidines, and to 2,6-disubstituted piperidines...
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