Tetrahedron Letters p. 2037 - 2040 (1995)
Update date:2022-08-11
Topics:
Golubev, Alexander
Sewald, Norbert
Burger, Klaus
Syntheses of 4-oxo-, cis-4-hydroxy-, and trans-4-hydroxy-L-pipecolic acids from L-aspartic acid using hexafluoroacetone as protecting reagent are described.Combination of a Stille cross-coupling reaction with subsequent Lewis acid catalyzed intramolecular Michael addition provides 4-oxo-L-pipecolic acid 5 or trans-6-methyl-4-oxo-L-pipecolic acid.Borohydride reduction of the protected 4-oxo-L-pipecolic acid derivative gives the corresponding cis-4-hydroxy-L-pipecolic acid 8.The trans isomer 10 is obtained in good yield via Mitsunobu inversion. - Key words: 4-Oxo-L-pipecolic acid, 4-hydroxy-L-pipecolic acids, L-aspartic acid, hexafluoroacetone, intramolecular Michael addition, Stille reaction
View MoreTianjin Hedong Red Cliff Chemical Reagent Factory
Contact:+86-022-84780548
Address:Li Ming Zhuang Gong Ye Yuan,Dongli District,Tianjin,China
Golden Union Agrochemical Import and Export Co., Ltd.
Contact:86-755-23910527
Address:Room 1106, Tower 3A, Excellence Century Center, Futian District, Shenzhen, China
NINGXIA DARONG CHEMICALS & METALLURGY CO.,LTD.
Contact:86-952-2179751
Address:Darong Road, Dawukou, Shizuishan, Ningxia 753001, China
Contact:0512-62706911
Address:No.289 Yinzhong South Road Wuzhong Economic Development District,Suzhou,China
Huangshi Shennong Chemical Technology Co., Ltd
Contact:+86-714-3072290
Address:Eastern industrial park , Tieshan district , Huangshi city ,Hubei province , China
Doi:10.1016/S0040-4039(01)89573-3
(1967)Doi:10.1016/S0031-9422(00)81596-4
(1986)Doi:10.1016/S0040-4020(97)00547-4
(1997)Doi:10.1021/jacs.5b02203
(2015)Doi:10.1002/anie.202012796
(2021)Doi:10.1055/s-0035-1560648
(2015)