Tetrahedron p. 403 - 412 (1989)
Update date:2022-08-03
Topics:
Kawashima, Masatoshi
Sato, Toshio
Fujisawa, Tamotsu
Organocopper reagents, such as diorganocuprates, organocopper-tributylphosphine, and Grignard reagents in the presence of a copper (I) salt, reacted with β-propiolactones by regioselective β-carbon-oxygen fission to give 3-substituted propionic acids.Among these three kinds of organocopper reagents, diorganocuprate, especially halomagnesium cuprate gave the highest yields of the acids, which was remarkably observed in the ring-opening of sterically hindered β-propiolactones such as β-methyl- and α,β-dimethyl-β-propiolactones and also in the reactions using the organocopper reagents with vinyl and allyl substituents.The ring-opening of β-propiolactone was confirmed to proceed by SN2 pathway with predominant inversion of configuration of the β-carbon by using the reaction of cis-α,β-dimethyl-β-propiolactone with di-tert-butylcuprate to afford syn-2,3,4,4-tetramethylpentanoic acid.
View Morewebsite:http://www.josunpharma.com
Contact:+86-311-80715268 80766839
Address:No.39, Zhaiying Street, Shijaizhuang,Hebei,China
Antaeus Bio-technology Co., LTD(expird)
Contact:021-31252569
Address:shanghai pudong
Contact:+44 7958 511245
Address:PO Box 469, Manchester, UK
Contact:+86-574- 87178138; 87297407
Address:No. 809, Liudingxingzuo, cangsong road, Ningbo, China
Contact:86-15972077575
Address:changzhou
Doi:10.1016/0008-6215(90)84108-7
(1990)Doi:10.1021/ja200879w
(2011)Doi:10.1039/c0ob00815j
(2011)Doi:10.1039/c39880001225
(1988)Doi:10.1080/10426507.2010.503211
(2011)Doi:10.1016/j.catcom.2015.06.002
(2015)