Another mode of heterocyclization of an enantiopure C-2-symmetric bis-epoxide leading to the symmetric dialkyl sulfide

作者：Xie, Weijia; Tanabe, Genzoh; Morimoto, Hiroyuki; Hatanaka, Takanori; Minematsu, Toshie; Wu, Xiaoming; Muraoka, Osamu^*

来源：Tetrahedron, 2010, 66(38): 7487-7491.

DOI：10.1016/j.tet.2010.07.064

• Heterocyclization
• Bis-epoxide
• Thiepane
• Thiepine
• Sodium sulfide

Reexamination of heterocyclization of an enantiopure C-2-symmetric bis-epoxide (7) with sodium sulfide is described. In addition to the reported processes leading to thiane (4a) and thiepane (6), another mode of cyclization was found to occur to a considerable extent, affording a symmetric dialkyl sulfide (5), and the structure of the main product reported (4a) has been revised. Conditions for the chemoselective formation of 6 were established, and effective transformation of 6 into 4 was accomplished by the modification of the processes.

• 出版日期2010-9-18
• 单位中国药科大学