Regiospecific and stereospecific synthesis of E-and Z-trisubstituted alkenes via 2, 2-disubstituted vinylsilanes

SSP Chou, HL Kuo, CJ Wang, CY Tsai…

Index: Chou, Shang-Shing P.; Kuo, Hwei-Lon; Wang, Chung-Jen; Tsai, Chung-Ying; Sun, Chung-Ming Journal of Organic Chemistry, 1989 ,  vol. 54,  # 4  p. 868 - 872

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Citation Number: 37

Abstract

Treatment of terminal alkynes 1 with the organocopper reagents derived from Grignard reagents, cuprous iodide, and lithium bromide (molar ratio 2: 1: 2) at low temperature followed by the addition of chlorotrimethylsilane gave the 2, 2-disubstituted vinylsilanes 2 with complete regio-and stereospecificity (syn addition). Electrophilic substitution of 2 with ICl, Brz, and acetyl chloride gave the corresponding vinyl iodides, bromides, and a,@- ...