Diastereoselective synthesis of 4, 5'-bis-proline compounds via reductive dimerization of N-acyloxyiminium ions
F Zanardi, A Sartori, C Curti, L Battistini…
Index: Zanardi, Franca; Sartori, Andrea; Curti, Claudio; Battistini, Lucia; Rassu, Gloria; Nicastro, Giuseppe; Casiraghi, Giovanni Journal of Organic Chemistry, 2007 , vol. 72, # 5 p. 1814 - 1817
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Citation Number: 12
Abstract
A short, practical synthesis of novel, unsymmetrical 4, 5'-bis-proline compounds has been achieved, highlighted by the application of an unprecedented samarium diiodide-driven regio-and diastereocontrolled reductive dimerization of N-acyloxyiminium ions generated from readily available 2-methoxy-5-silyloxymethyl-N-Boc pyrrolidines. The title proline dimers proved to be pertinent metal-free catalysts in aldol and Mannich reactions.
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