Asymmetric carbon-carbon bond formations in conjugate additions of lithiated N-Boc allylic and benzylic amines to nitroalkenes: enantioselective synthesis of …

…, DO Jang, BW Slafer, MD Curtis, P Beak

Index: Johnson, Timothy A.; Jang, Doo Ok; Slafer, Brian W.; Curtis, Michael D.; Beak, Peter Journal of the American Chemical Society, 2002 , vol. 124, # 39 p. 11689 - 11698

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Citation Number: 88

Abstract

(-)-Sparteine mediated lithiations of N-Boc-allylic and benzylic amines provide configurationally stable intermediates which on conjugate additions to nitroalkenes provide highly enantioenriched enecarbamate products in good yields, and with high diastereoselectivities. Straightforward transformations of these adducts offer general routes to substituted 3, 4-substituted piperidines, 3, 4-substituted pyrrolidines, and 4, 5- ...