Direct introduction of glycine/mercaptoacetic acid units into electron-poor alkenes: a novel route to functionally rich alpha-amino/alpha-mercapto acids

作者：Yadav Lal Dhar S^*; Rai Ankita

来源：Tetrahedron Letters, 2008, 49(40): 5751-5754.

DOI：10.1016/j.tetlet.2008.07.103

• alpha-amino acids
• alpha-mercapto acids
• Michael addition
• Lewis acid
• stereoselective synthesis
• activated alkenes

The first example of an operationally simple direct introduction of glycine/mercaptoacetic acid units into electron-poor alkenes is reported. In this protocol, Lewis acid-catalyzed Michael addition of activated glycine or mercaptoacetic acid, that is 2-phenyl-1,3-oxazol-5-one or 2-methyl-2-phenyl-1,3-oxathiolan-5-one, to various electron-poor alkenes in water/1,4-dioxane (1:2, v/v) solvent system diastereoselectively affords the corresponding functionally rich alpha-amino acids or alpha-mercapto acids, respectively, in high yields at ambient temperature.

• 出版日期2008-9-29