Journal of the Chemical Society. Perkin transactions I p. 2639 - 2646 (1988)
Update date:2022-08-05
Topics:
Padwa, Albert
Carter, Stephen P.
Chiacchio, Ugo
Kline, Donald N.
Perumattam, John
1,3-Dipolar cycloaddition of nitrones to phenylsulphonylallene gives in high yield and with complete regiospecificity 5-methyleneisoxazolidines.These on treatment with base and subsequent reaction with electrophiles afford both α- and γ-substituted products.With methyl iodide as the electrophile, only the α-methylated product was isolated.In contrast, reaction of the 5-exo-methylene-4-phenylsulphonylisoxazolidine with allyl bromide afforded the γ-allyated product.Formation of this was shown to be via direct γ-attack, rather than by α-attack, followed by a 3,3-sigmatropic rearrangement.Further studies show that the product ratio is controlled by a sensitive interplay between thermodynamic and steric factors and is very dependent on the nature of the electrophile used.
View MoreContact:+86-571-87859231, 87859237, 87859239
Address:1606,Huarong Times Mansion, No.3880 Jiangnan Avenue, Binjiang District, Hangzhou, China, 310053
Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd
website:http://www.jlpharms.com
Contact:86-571-86982636
Address:Rm A606, Fuyi Center, jianqiao street
Shanghai Sungo Technology Chemical Co., Ltd
Contact:0086-21-51385579
Address:Room2010, F/20, Tonghua Plaza, NO 345 Jinxiang Road, Jinqiao Export Processing Zone, Shanghai, 201206 P.R.CHINA
Tianjin Bright Future Technology Co., Ltd
Contact:0086-22-58016666
Address:NO.136 DongTeng Lake Street Tianjin Economic and Technology Development Area,Tainjin,China
Xinji City Taida Sinopec Co., Ltd.
Contact:0086-311-85341278
Address:No.6, Nanhua Road,Xinji City Road,Hebei Province,China
Doi:10.1021/acs.jmedchem.1c00440
(2022)Doi:10.1016/j.molstruc.2013.03.013
(2013)Doi:10.1007/BF00962517
(1988)Doi:10.1021/acs.orglett.7b02124
(2017)Doi:10.1002/ejoc.201101598
(2012)Doi:10.1021/jo00268a026
(1989)
