Journal of Organic Chemistry p. 5458 - 5462 (1994)
Update date:2022-07-29
Topics:
Prandi, Cristina
Venturello, Paolo
The reaction of (E)-1,1-diethoxybut-2-ene (1a) and 1,1-diethoxy-3-methylbut-2-ene (1b) with 2 equiv of sec-butyllithium complexed with potassium tert-butoxide (Schlosser's base) in THF at -95 deg C gives 1-metalated 1-ethoxy 1,3-dienes that are synthetically equivalent to acyl anions.Subsequent reaction with suitable electrophiles, such as alkyl halides, aldehydes, ketones, carbon dioxide, and carboxylic acid derivatives, affords (E)-1-substituted 1-ethoxy 1,3-dienes 2a-i.Experimental procedures are given for the reaction of the carbanionic intermediates with the electrophiles.Some typical examples for the conversion of the produced α-substituted alkoxy dienes into the corresponding α,β-unsaturated carbonyl compounds are also reported.In particular, in the case in which crotonaldehyde is used as an electrophile, the addition product 2c undergoes acid-catalyzed conversion to compounds 4c, 5c, and 6c as a function of the experimental conditions.
View MoreContact:+86-575-82733999 0575-82732999
Address:hangzhou gulf fine chemical zone,shangyu city,zhejiang province
JinTan Pingsheng Chemical Co.,Ltd
Contact:+86-519-82828200
Address:NO.11Danfengxilu Road,Jintan City,Jiangsu,China
Beijing Mesochem Technology Co.,LTD
website:http://www.mesochem.com
Contact:0086-10-57862036
Address:2301, Floor 23, Building 9 Lippo Plaza, Yard 8 Ronghua Middle Road, ETDZ, Beijing, China
Shanghai Mintchem Development ., Ltd
Contact:0086 21 5190 8570
Address:R602,4#,89Nong, Mudan Road Pudong Shanghai China
Shanghai Coupling Pharmaceutical R&D Co., Ltd.
Contact:+86 021 50106671
Address:403 Room No.4 Buiding, No. 526 Ruiqing Road, Shanghai Zhangjiang Hi-Tech Park
Doi:10.1002/anie.201308486
(2014)Doi:10.1021/acs.orglett.9b01675
(2019)Doi:10.1246/bcsj.40.2129
(1967)Doi:10.1039/c3dt52838c
(2014)Doi:10.1016/j.ejmech.2014.01.024
(2014)Doi:10.1039/b921169a
(2010)