Tetrahedron Letters p. 7997 - 8000 (2003)
Update date:2022-08-03
Topics:
McCormick, Jinping L.
Osterman, Rebecca
Chan, Tze-Ming
Das, Pradip R.
Pramanik, Birendra N.
Ganguly, Ashit K.
Girijavallabhan, Viyyoor M.
McPhail, Andrew T.
Saksena, Anil K.
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.
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