Diastereoselective synthesis of 4,5'-bis-proline compounds via reductive dimerization of N-acyloxyiminium ions |
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Authors: | Zanardi Franca Sartori Andrea Curti Claudio Battistini Lucia Rassu Gloria Nicastro Giuseppe Casiraghi Giovanni |
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Affiliation: | Dipartimento Farmaceutico, Università degli Studi di Parma, Viale G.P. Usberti 27A, I-43100 Parma, Italy. |
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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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