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 MoreBrightGene Bio-Medical Technology Co., Ltd.
website:https://en.bright-gene.com/
Contact:+86-512-62551801
Address:Building C25 - C31, No. 218 Xinghu Road, Suzhou Industrial Park, Suzhou, Jiangsu, China.
HANGZHOU TOYOND BIOTECH CO., LTD
Contact:+86-571-86965177
Address:No. 189, Fengqi East Road, Hangzhou, China
Guangxi Shanyun Biochemical Science and Technology Co., Ltd
Contact:+86-0772--6828887
Address:#2 Industrial Park of Luzhai County, Liuzhou, Guangxi, China
Contact:+86-571-86491666
Address:SHI XIANG ROAD
Shaanxi King Stone Enterprise Company Limited
Contact:86-29-88353805,13609285751
Address:.209 Keji Road Hi-Tech industrial Develpment Zone .Xian 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)
