A highly stereoselective approach to novel 2,2,4-trisubstituted pyrrolidines by halocylization: Key intermediates towards syntheses of nitrogen analogs of Noxafil®
A convenient synthesis of novel 2,2,4-trisubstituted pyrrolidines via stereoselective 5-exo iodocyclization of the 2,2-disubstituted olefins 8 and 9 is described. Single crystal X-ray analysis of the oxazolidinone 15 confirmed the relative stereochemistry in this cyclization. As observed earlier in the formation of 2,2,4-trisubstituted tetrahydrofurans, the presence of a bulky aryl substituent on the olefin appears to direct the stereochemical outcome of these halocyclizations. © 2003 Elsevier Ltd. All rights reserved.
McCormick, JL; Osterman, R; Chan, TM; Das, PR; Pramanik, BN; Ganguly, AK; Girijavallabhan, VM; McPhail, AT; Saksena, AK
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