One-pot synthesis of β-N-glycosyl imidazole analogues via a palladium-catalysed decarboxylative allylation

被引：25

作者：

Xiang, Shaohua ^{[1
]}

He, Jingxi ^{[1
]}

Ma, Jimei ^{[1
]}

Liu, Xue-Wei ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 32期

关键词：

ALLYLIC ALKYLATION; C-GLYCOSYLATION; ASPARAGINE CONJUGATE; BOND FORMATION; GLYCALS; KETONES; GLYCOBIOLOGY; CYCLIZATION; ACCESS;

D O I：

10.1039/c3cc48041k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise and highly efficient strategy for the synthesis of N-glycosyl imidazole analogues is reported. This reaction is based on a palladium catalysed decarboxylative allylation and three steps, namely, carbamation, decarboxylation and allylation are involved. All the substrates can afford the desired products with excellent yields and selectivities.

引用

页码：4222 / 4224

页数：3

共 50 条

[1] One-pot palladium-catalysed synthesis of molecular wires
Fraysse, S
Coudret, C
Launay, JP
TETRAHEDRON LETTERS, 1998, 39 (43) : 7873 - 7876
[2] One-pot palladium-catalysed synthesis of sulfonyl fluorides from aryl bromides
Davies, Alyn
Curto, John
Bagley, Scott
Willis, Michael
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[3] Stereoselective synthesis of (-)-trachelanthamidine via palladium-catalysed intramolecular allylation
Craig, Donald
Hyland, Christopher J. T.
Ward, Simon E.
SYNLETT, 2006, (13) : 2142 - 2144
[4] Stereoselective γ-lactam synthesis via palladium-catalysed intramolecular allylation
Craig, D
Hyland, CJT
Ward, SE
CHEMICAL COMMUNICATIONS, 2005, (27) : 3439 - 3441
[5] One-Pot Synthesis of Carbamoyl Azides via Palladium-Catalysed Azidocarbonylation of Haloarenes Using N-Formylsaccharin as a CO Surrogate
Yadav, Vinod K.
Srivastava, Vishnu P.
Yadav, Lal Dhar S.
SYNLETT, 2016, 27 (20) : 2826 - 2830
[6] One-Pot Palladium(II)-Catalyzed Synthesis of Fluorenones via Decarboxylative Cyclization
Cai, Zhiqiang
Hou, Xu
Hou, Ling
Hu, Zhiquan
Zhang, Bo
Jin, Zhengsheng
SYNLETT, 2016, 27 (03) : 395 - 398
[7] Palladium-catalysed coupling of two imines and acid chloride: A direct one-pot synthesis of imidazoles
Siamaki, Ali R.
Arndtsen, Bruce A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3250 - U3250
[8] Synthesis of chiral and achiral analogues of ambroxol via palladium-catalysed reactions
Jornal of the Chemical Society. Perkin Transactions 1, (19):
[9] Synthesis of chiral and achiral analogues of ambroxol via palladium-catalysed reactions
Larsson, ALE
Gatti, RGP
Backvall, JE
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (19): : 2873 - 2877
[10] One-Pot Synthesis of Cyclopentenols from Vinylethylene Carbonates via Palladium-Catalyzed Decarboxylative Allylation and Cascade Oxidation-Cyclization
Zhang, Ke
Ke, Miaolin
Liu, Zhigang
Zuo, Sheng
Fen-er Chen
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2022, 95 (04) : 634 - 638

← 1 2 3 4 5 →