An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates

作者：Lach Slawomir; Demkowicz Sebastian; Witt Dariusz^*

来源：Tetrahedron Letters, 2013, 54(51): 7021-7023.

DOI：10.1016/j.tetlet.2013.10.056

• Unsymmetrical disulfides
• Thiolate
• Phosphorodithioic acid
• Thioacetates
• Biotin

We have developed convenient methods for the synthesis of functionalized unsymmetrical dialkyl disulfides under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives 1 with functionalized alkyl thiolate anions, generated in situ from thioacetates 2 and sodium methoxide or butylamine. The developed method allows the preparation of unsymmetrical disulfides bearing additional hydroxy, carboxy, amino, azido, biotin, or maleimide functionalities.

• 出版日期2013-12-18