Monissa C Paderes1, Sherry R Chemler. 1. Department of Chemistry, University at Buffalo, The State University of New York, 618 Natural Sciences Complex, Buffalo, New York 14260, USA.
Abstract
The diastereoselectivity of the copper-promoted intramolecular aminooxygenation of various alkene substrates was investigated. Alpha-substituted 4-pentenyl sulfonamides favor the formation of 2,5-cis-pyrrolidines (dr >20:1) giving excellent yields which range from 76-97% while gamma-substituted substrates favor the 2,3-trans pyrrolidine adducts with moderate selectivity (ca. 3:1). A substrate whose N-substituent was directly tethered to the alpha-carbon exclusively yielded the 2,5-trans pyrrolidine. The synthetic utility of the method was demonstrated by a short and efficient formal synthesis of (+)-monomorine.
The diastereoselectivity of the copper-promoted intramolecular aminooxygenation of various n class="Chemical">alkene substrates was investigated. Alpha-substituted 4-pentenyl sulfonamides favor the formation of 2,5-cis-pyrrolidines (dr >20:1) giving excellent yields which range from 76-97% while gamma-substituted substrates favor the 2,3-trans pyrrolidine adducts with moderate selectivity (ca. 3:1). A substrate whose N-substituent was directly tethered to the alpha-carbon exclusively yielded the 2,5-trans pyrrolidine. The synthetic utility of the method was demonstrated by a short and efficient formal synthesis of (+)-monomorine.
Authors: Timothy J Donohoe; Majid J Chughtai; David J Klauber; David Griffin; Andrew D Campbell Journal: J Am Chem Soc Date: 2006-03-01 Impact factor: 15.419
Authors: Shuklendu D Karyakarte; Fatima C Sequeira; Garrick H Zibreg; Guoqing Huang; Josiah P Matthew; Marina M M Ferreira; Sherry R Chemler Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415