Journal of the Chemical Society. Perkin transactions I p. 1047 - 1054 (1990)
Update date:2022-08-04
Topics:
Kennedy, Michael
McKervey, M. Anthony
Maguire, Anita R.
Tuladhar, Sarbajna M.
Twohig, M. Fiona
Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclo<5.3.0>decatrienones or 2-tetralones depending on the substitution pattern of the aryl ring in the precursor; the former products are transformed into the latter catalytically with trifluoroacetic acid.Precursors with methyl, methoxy, and acetoxy substituents have been examined, efficient cyclisation occurring in all cases.When the precursor contains a meta-methoxy substituent, 2-tetralones are obtained directly.The efficient conversion of 3-phenylpropionicacid into trans-1-methylbicyclo<5.3.0>decan-2-one is also described, partial asymmetric synthesis having been realised through the use of rhodium (S)-mandelate as the cyclisation catalyst.Cyclisations of diazoketones derived from 4-phenylbutyric acid and 5-phenylpentanoic acid have also been studied; the former provides a new entry into the bicyclo<5.4.0>undecane system whereas the latter produces a 2,3-disubstituted cyclopentanone via C-H insertion.Aspects of the cycloheptatriene-norcaradiene equilibrium in fused ring systems are discussed.
View MoreContact:+86-0512-69209969
Address:Room 317,Lushan Road,Suzhou New District,Jiangsu Province,China.
Shandong Xinke Petrochemical Co., Ltd.
Contact:+86-546-7277016
Address:Gudao Industrial Park, Hekou District, Dongying, Shandong Province, China
Contact:+44 (0)2036089360-31
Address:Chanceryhouse,Chancery Lan
Contact:86-516-66656369
Address:The west road of Huaihai, Xuzhou, China
SHAANXI FUJIE PHARMACEUTICAL CO.,LTD
website:http://www.fujiepharm.com
Contact:+86-29-63650906
Address:Yuanqu Yi Road, Qinghe Food Industrial Park, Sanyuan County, Shaanxi Province, China
Doi:10.1021/jm049924d
(2004)Doi:10.1016/S0040-4039(01)95014-2
(1978)Doi:10.1016/j.tetlet.2004.02.117
(2004)Doi:10.1007/s10870-016-0640-4
(2016)Doi:10.1016/0040-4020(78)87007-0
(1978)Doi:10.1016/j.ica.2003.11.026
(2004)
