e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Asymmetric synthesis of axially chiral, unsymmetrical diphenic acids via intramolecular Ullmann coupling reaction

…, H Fukushima, S Handa, H Ito, H Hashimoto

Index: Miyano, Sotaro; Fukushima, Hiroshi; Handa, Shigeru; Ito, Hiromitsu; Hashimoto, Harukichi Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 3249 - 3254

Full Text: HTML

Citation Number: 61

Abstract

A practical route to unsymmetrical diphenic acids is described. Successive esterification of ethylene glycol with two different 2-halobenzoyl chlorides gave the corresponding mixed diester, which was treated with copper powder in boiling DMF under dilution conditions. Silica-gel column chromatography allowed ready separation of the intramolecularly coupled cyclic diester (30–60% yield) from other by-products accompanying the Ullmann reaction, ...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-((2-iodo-3-n...

~81%

14,16-dichloro-17-nitrodibenzo[h,j]dinaphtho[2,1-b:1',2'-d][1,6]dioxacyclododecine-12,21-dione Structure

14,16-dichloro-...

2'-hydroxy-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-hydroxy-[1,1...

~%

14,16-dichloro-17-nitrodibenzo[h,j]dinaphtho[2,1-b:1',2'-d][1,6]dioxacyclododecine-12,21-dione Structure

14,16-dichloro-...

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

~%

14,16-dichloro-17-nitrodibenzo[h,j]dinaphtho[2,1-b:1',2'-d][1,6]dioxacyclododecine-12,21-dione Structure

14,16-dichloro-...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

~%

14,16-dichloro-17-nitrodibenzo[h,j]dinaphtho[2,1-b:1',2'-d][1,6]dioxacyclododecine-12,21-dione Structure

14,16-dichloro-...

2'-hydroxy-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-hydroxy-[1,1...

~%

19,21-dichlorobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19,21-dichlorob...

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

~%

19,21-dichlorobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19,21-dichlorob...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

~%

19,21-dichlorobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19,21-dichlorob...

2'-hydroxy-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-hydroxy-[1,1...

~%

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

19,21-dichlorobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19,21-dichlorob...

~%

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

14,16-dichloro-17-nitrodibenzo[h,j]dinaphtho[2,1-b:1',2'-d][1,6]dioxacyclododecine-12,21-dione Structure

14,16-dichloro-...

~%

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-((2-iodo-3-n...

~%

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

~%

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-((2-iodo-3-n...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

~%

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-((2-iodo-3-n...

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

~%

2'-hydroxy-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-hydroxy-[1,1...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

~%

2'-hydroxy-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-hydroxy-[1,1...

2'-((2-iodo-3-nitrobenzoyl)oxy)-[1,1'-binaphthalen]-2-yl 1-bromo-2-naphthoate Structure

2'-((2-iodo-3-n...

~47%

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

2'-hydroxy-[1,1'-binaphthalen]-2-yl 3,5-dichloro-2-iodobenzoate Structure

2'-hydroxy-[1,1...

~%

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

19,21-dichlorobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19,21-dichlorob...

~%

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...

14,16-dichloro-17-nitrodibenzo[h,j]dinaphtho[2,1-b:1',2'-d][1,6]dioxacyclododecine-12,21-dione Structure

14,16-dichloro-...

~%

19-nitrobenzo[h]trinaphtho[2,1-b:1',2'-d:1'',2''-j][1,6]dioxacyclododecine-12,23-dione Structure

19-nitrobenzo[h...