Chemical and Pharmaceutical Bulletin p. 1094 - 1101 (1998)
Update date:2022-08-03
Topics:
Itaya, Taisuke
Hozumi, Yoshitaka
Phenyl, tolyl, anisyl, and 1-naphthyl iodides (7a-g,n) smoothly reacted with (S)-N-(benzyloxycarbonyl)-vinylglycine (6) in H2O in the presence of Pd(OAc)2, Bu4NCI, and NaHCO3 at 45°C, producing [S-(E)]-(2- arylvinyl)glycine derivatives 8a-g, n of high enantiomeric purity. The yields of the reactions of 3- (7f), 2- (7e), and 4-iodoanisoles (7g) increased in this order. This relationship between the yield and the position of substitution has been found to hold for bromophenyl iodides (7i-k), although somewhat lower chemical and optical yields were realized in these cases. Phenyl iodide 71 carrying an electron-withdrawing 4-acetyl group gave an unsatisfactory result, and more electron-deficient 4-nitrophenyl iodide (7m) did not provide the desired product. All these results suggest that the reaction is advantageous with electron-sufficient substrates 7. However, this was not the case for 4-iodophenol (7h), as well as some heterocyclic iodides.
View MoreKunming Biohome Technology Co. Ltd.
website:http://www.biohometech.com/
Contact:86-871-67428869
Address:kunming
Contact:86-25-84683399
Address:605, Phoenix Herui Plaza, No.389, South Taiping Road, Nanjing, China 210002
Contact:0311-13263231263
Address:jian hua street,Shijiazhuang City, China
Mollt Biochem Co., Ltd(expird)
Contact:+86-21-38682181
Address:shanghai ,china
ANHUI CHEM-BRIGHT BIOENGINEERING CO.,LTD
Contact:86-561-4080321
Address:No.8 Lieshan Industrial Zone of Huaibei
Doi:10.1016/j.bmcl.2005.01.078
(2005)Doi:10.1016/S0022-328X(98)00649-4
(1998)Doi:10.1016/S0960-894X(03)00668-1
(2003)Doi:10.1002/chem.201601044
(2016)Doi:10.1080/10426509708031609
(1997)Doi:10.1021/om980157o
(1998)
