Tetrahedron letters

Dithioacetal as a 1, 1-zwitterion synthon. Synthesis of functionalized alkenes by the coupling of benzylic dithioacetals with another 1, 1-zwitterion synthon

HY Tu, YH Liu, Y Wang, TY Luh

Index: Tu, Hai-Yang; Liu, Yi-Hung; Wang, Yu; Luh, Tien-Yau Tetrahedron Letters, 2005 , vol. 46, # 5 p. 771 - 773

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Citation Number: 6

Abstract

Direct coupling of a 1,1-zwitterion synthon with another kind of 1,1-zwitterion synthon appears to be an attractive route for the synthesis of carbon–carbon double bond. It is well documented that the dithioacetal functionality can serve as a dication synthon. 1 In the presence of a catalytic amount of NiCl 2 (PPh 3 ) 2 , benzylic or allylic dithioacetals react with Grignard reagents to give the corresponding olefination products (Eq. 1). 1 The reaction can also proceed with ...