Tetrahedron p. 9365 - 9376 (1994)
Update date:2022-09-26
Topics:
Hunter, Roger
Michael, Joseph P.
Simon, Clive D.
Walter, Daryl S.
Pummerer-derived substituted vinylthionium ions (allyl phenyl sulfoxide, TMSOTf, EtN(i-Pr)2, CH2Cl2, -78 deg C) with a β-trimethylsilylmethyl (2), γ-phenyl (14), or γ-phenylthio (15) group allylate the enol silyl ethers of acetophenone (3) and cyclohexanone (4) in good yield.Allylation with (14) and (15) required slow addition of base in order to limit the rate of production of intermediate, and thus avoid unwanted sila-Pummerer type products.Huenigs's base conjugate addition was not observed in these cases.Both the (E)- and (Z)- forms of allyl sulfoxide (15) were shown to equilibrate to the (E)-transoid conformer prior to allylation resulting in exclusive (E)-vinyl sulfide formation.Blocking of the γ-position resulted in preferential α-attack.
View MoreShanghai Rich Chemicals Co., Ltd
website:http://www.richchemical.com
Contact:+86-21-20255798
Address:Pudong Shanghai,China
Shanghai Yudiao Chemistry Technology Co.,Ltd
Contact:0086-18964703211
Address:Building NO.5, NO.218,Rongtian Road,ganxiang town,Jinshan District,shanghai,201518,china
Shanghai Yuking Water Soluble Material Tech Co., Ltd
Contact:86-21-68286299
Address:4F, 13B, No. 600, South Xinyuan Road 201306, Shanghai, China
website:http://www.china-sinoway.com
Contact:+86-592-5853819
Address:16/F,Huicheng Comm,Complex,No839 XiaHe Rd, Xiamen,China
Contact:+86+21-58956006 15800617331
Address:402 Room, 150# Cailun Road, Zhangjiang high tech park, Shanghai
Doi:10.1016/j.tetasy.2007.10.019
(2007)Doi:10.1021/jm301053a
(2012)Doi:10.1016/0957-4166(95)00155-I
(1995)Doi:10.1016/S0040-4020(03)00827-5
(2003)Doi:10.1021/jo035689f
(2004)Doi:10.1021/ic030151d
(2003)
