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Enantioselective protecting group-free synthesis of 1-S-ethyl-4-substituted quinolizidines
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A practical enantioselective protecting group-free four-step route to the key quinolizidinone 6 from phenylglycinol-derived bicyclic lactam 1 is reported. The Grignard addition reaction to 6 takes place stereoselectively to give 1-ethyl-4-substituted quinolizidines 4-epi-207I and 7-9. Following a similar synthetic sequence, 9a-epi-6 is also accessed. However, the addition of Grignard reagents to 9a-epi-6 proceeds in a non-stereoselective manner. In order to gain insight into the different stereochemical outcome in the two series, theoretical calculations on the iminium salts A and B have been performed. The study concludes that the addition of the hydride, which is the step that determines the configuration of the final products, occurs in a stereoelectronic controlled manner. The theoretical study is in agreement with the experimental results.
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AMAT TUSÓN, Mercedes, et al. Enantioselective protecting group-free synthesis of 1-S-ethyl-4-substituted quinolizidines. Organic & Biomolecular Chemistry. 2012. Vol. 10, num. 6866-6875. ISSN 1477-0520. [consulted: 3 of August of 2026]. Available at: https://hdl.handle.net/2445/127646