Journal of Organic Chemistry p. 4639 - 4642 (1990)
Update date:2022-08-04
Topics:
Thenappan, Alagappan
Burton, Donald J.
A reduction-olefination sequence has been used to convert esters to α-fluoro α,β-unsaturated esters.In the presence of diisobutylaluminum hydride, esters are reduced to aldehydes that react in situ with <(EtO)2P(O)CFC(O)Et>-Li+ to form the title compounds in good yield with high stereoselectivity.The reaction is applicable to aliphatic, aromatic, cyclic, unsaturated, perfluorinated, and partially fluorinated esters.The E/Z ratio of unsaturated esters formed in the reaction varies with the cations present in the reaction mixture.Solvents have very little influence on stereochemistry.The sequential transformation of PhC(O)OBun to (E)-PhCH=CFC(O)OEt and then to (E,E)-PhCH=CFCH=CFC(O)OEt illustrates the scope of this methodology, which introduces a fluorine atom adjacent to an ester functionality with concomitant elongation of the chain by two carbon atoms.
View MoreContact:0091-265-2313036
Address:311, ATLANTIS HEIGHTS SARABHAI MAIN ROAD,VADIWADI ,VADODARA
Contact:886 2 2541 0022
Address:8 Fl., No. 11, Sec. 1, Chung Shan North Rd., Taipei, Taiwan R.O.C.
Basilea Pharmaceutica China Ltd.
Contact:+86-513-82198075
Address:No.638 Xiushan Road(East),Haimen, Jiangsu 226100, P.R.China
Guilin Zhenda Bio-Tech Co., Ltd.
Contact:86-773-3568977
Address:-Yangtang shangshui industry park, Lingui county,
Hangzhou Yingshanhua Pigment Chemicals Co.,Ltd.
Contact:+86-0150-58101658
Address:Nanyang Economic DevelopmentZong,Xiaoshan,Hangzhou,China
Doi:10.1016/j.bmcl.2020.127502
(2020)Doi:10.1016/j.tet.2015.08.040
(2015)Doi:10.1039/c003734f
(2010)Doi:10.1002/chem.201000241
(2010)Doi:10.1007/BF00958060
(1989)Doi:10.1039/C39900001018
(1990)