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Stereodivergent Access to Cis- and Trans-3,5-Disubstituted 1,4-Thiazane 1‑Oxides by Cyclization of Homochiral β‑Amino Sulfoxides and Sulfones. The Preparation of Isomeric Ant Venom Alkaloids

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journal contribution
posted on 18.02.2016, 22:58 by Stefan C. Söderman, Adrian L. Schwan
Intramolecular conjugate additions of homochiral (E)-1-alkenyl 2-aminoalkyl sulfoxides and sulfones were investigated. The relative position of the 3,5-substituents of the resulting 1,4-thiazane oxides was found to be dependent on the oxidation state of the sulfur atom, demonstrating a simple and highly stereodivergent synthetic protocol. Selected cis- and trans-3,5-disubstituted 1,4-thiazane dioxides were converted to cis- and trans-2,5-disubstituted pyrrolidines, known ant venom alkaloids.