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

作者：Soederman Stefan C; Schwan Adrian L^*

来源：Organic Letters, 2013, 15(17): 4434-4437.

DOI：10.1021/ol4023003

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.

• 出版日期2013-9-6