AK-1984GU_published_mainmanuscript - Issue in Honor of Prof...

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Issue in Honor of Prof. Alain Krief ARKIVOC 2007 (x) 10-20 Recent Advances in Bismuth Mediated Aldol and Mannich Reactions Thierry Ollevier,* Valerie Desyroy, and Etienne Nadeau Département de chimie, Université Laval, Québec (Québec) G1K 7P4, Canada E-mail: [email protected] Dedicated to Professor Alain Krief on the occasion of his 65 th birthday Abstract Bismuth metal and bismuth salts have been used for various aldol and Mannich type reactions. Bismuth(III) salts, and bismuth(III) triflate in particular, are cheap and environmentally benign Lewis acids. This account highlights the scope and applications of bismuth(0) and bismuth(III) salts in fundamental reactions like the aldol and Mannich reactions. Various bismuth mediated Mukaiyama aldol and Mannich type reactions are presented. Bismuth(0) mediated Reformatsky and imino Reformatsky reactions are also disclosed in this account. Keywords: Bismuth, Bismuth triflate, Aldol, Mukaiyama aldol, Mannich, Multicomponent reactions, Green chemistry Contents 1. Introduction 2. Bismuth mediated aldol reactions 2.1 Bismuth(III) catalyzed Mukaiyama aldol reactions 2.2 Bismuth(0) mediated Reformatsky reactions 3. Bismuth mediated Mannich type reactions 3.1 Bismuth(III) catalyzed Mannich type reactions 3.1.1 One pot bismuth(III) catalyzed Mannich type reactions 3.1.2 Bismuth(III) catalyzed Mannich type reactions with nitriles 3.2 Bismuth(III) catalyzed Mannich type reactions of N -alkoxycarbonylamino sulfones 3.3 Bismuth(III) catalyzed aziridination reactions 3.4 Bismuth(III) mediated homo Mannich type reactions 3.5 Bismuth(0) mediated imino Reformatsky reactions 4. Conclusions 5. References ISSN 1424-6376 Page 10 © ARKAT-USA, Inc.
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