Journal of Organic Chemistry p. 879 - 886 (1993)
Update date:2022-08-04
Topics:
Koskinen, Ari M. P.
Munoz, Luis
tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields.The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclo<3.1.0>hexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 15 via Curtius- or Hoffmann-type rearrangements, respectively.The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40percent overall from malonic acid).The free amino acids 12 and 13 can be liberated in two steps.
View MoreContact:+86-512-69561895
Address:No.111, Building A4, 218 Xinghu Street, Suzhou Industrial Park, P. R. China
Contact:+1-416-493-6870
Address:Toronto, Canada
Jining Shengrun Chemical Industry Co., Ltd.
Contact:+86-537-7121666 ,
Address:West Ring Road,Wenshang County Shandong Province
Hebei Kangtai Pharmaceutical Co.,Ltd
Contact:+86-0317-3512963
Address:Wugang Road,Mengcun of Cangzhou City,Hebei Province ,China
Contact:+86 512 6287 2180
Address:398 Ruoshui Road, Suzhou Industrial Park, Suzhou, Jiangsu, P. R. China
Doi:10.1002/pola.24641
(2011)Doi:10.1016/0022-328X(90)87300-3
(1990)Doi:10.1016/S0040-4039(00)88864-4
(1990)Doi:10.1039/c0cc05646d
(2011)Doi:10.1002/asia.201801193
(2018)Doi:10.1002/chem.201002888
(2011)