title: 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.
abstract: 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.
authors: Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1.
authors: Stefan C
authors: SC
authors: Söderman
authors: Adrian L
authors: AL
authors: Schwan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D000862:Ant Venoms / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000862:Ant Venoms; D011759:Pyrrolidines; D013450:Sulfones; D013454:Sulfoxides