Superacid-Promoted Reactions of N-Acyliminium Ions: An effective route to substituted 3-Oxo-1, 2, 3, 4-tetrahydroisoquinolines and related products

…, PJ Kindelin, DJ DeSchepper, C Zheng, DA Klumpp

Index: Zhang, Yiliang; Kindelin, Patrick J.; DeSchepper, Daniel J.; Zheng, Chong; Klumpp, Douglas A. Synthesis, 2006 , # 11 p. 1775 - 1780

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Citation Number: 6

Abstract

Abstract Intramolecular cyclizations involving N-acyliminium ions are shown to give products in good yields from reactions with CF 3 SO 3 H (triflic acid). The resulting 3-oxo-1, 2, 3, 4- tetrahydroisoquinolines have been converted in high yields to 1, 2-diaryl-1, 2, 3, 4- tetrahydroisoquinolines, which have been recently shown to be selective estrogen receptor modulators. In a reaction using a chiral N-acyliminium ion, cyclization is found to occur in ...