Enantio‐ and Diastereoconvergent Cyclocondensation Reactions: Synthesis of Enantiopure cis‐Decahydroquinolines |
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| Authors: | Prof Dr Mercedes Amat Elena Ghirardi Dr Laura Navío Dr Rosa Griera Dr Núria Llor Dr Elies Molins Prof Dr Joan Bosch |
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| Institution: | 1. Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona (Spain);2. Institut de Ciència de Materials de Barcelona (CSIC), Campus UAB, 08193 Cerdanyola (Spain) |
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| Abstract: | Up to four stereocenters with a well‐defined configuration are generated in a single synthetic step by the cyclocondensation of (R)‐phenylglycinol or (1S,2R)‐1‐amino‐2‐indanol with stereoisomeric mixtures (racemates, meso forms, diastereoisomers) of cyclohexanone‐based δ‐keto‐acid and δ‐keto‐diacid derivatives in enantio‐ and diastereoconvergent processes that involve dynamic kinetic resolution and/or desymmetrization of enantiotopic groups. A detailed analysis of the stereochemical outcome of this process is presented. This method provides easy access to enantiopure 8‐ and 6,8‐substituted cis‐decahydroquinolines, including alkaloids of the myrioxazine family. |
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| Keywords: | alkaloids asymmetric synthesis diastereoselectivity lactams nitrogen heterocycles |
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