Arylsulfonate esters in solid phase organic synthesis. I. Cleavage with amines, thiolate, and imidazole

被引：60

作者：

Rueter, JK ^{[1
]}

Nortey, SO ^{[1
]}

Baxter, EW ^{[1
]}

Leo, GC ^{[1
]}

Reitz, AB ^{[1
]}

机构：

[1] RW Johnson Pharmaceut Res Inst, Drug Discovery Div, Spring House, PA 19477 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(97)10719-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The arylsulfonate ester functionality connecting an alkyl chain to a polystyrene resin is cleaved with neat volatile primary or secondary amines to give secondary or tertiary amines, respectively, in high yields and purity. Non-volatile secondary amines, thiols, and imidazole also cleave the alkyl chain efficiently to afford the expected products which can be readily purified by an ion-exchange resin work-up method. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：975 / 978

页数：4

共 25 条

[1] Hermkens, P.H.H., Ottenheijm, H.C.J., Rees, D.C., (1997) Tetrahedron, 53, pp. 5643-5678
[2] Hermkens, P.H.H., Ottenheijm, H.C.J., Rees, D., (1996) Tetrahedron, 52, pp. 4527-4554
[3] Balkenhohl, F., Von Dem Bussche-Hünnefeld, C., Lansky, A., Zechel, C., (1996) Angew. Chem. Int. Ed. Engl., 35, pp. 2288-2337
[4] Früchtel, J.S., Jung, G., (1996) Angew. Chem. Int. Ed. Engl., 35, pp. 17-42
[5] Fenniri, H., (1996) Curr. Med. Chem., 3, pp. 343-378
[6] Thompson, L.A., Ellman, J.A., (1996) Chem. Rev., 96, pp. 555-600
[7] Gordon, E.M., Barrett, R.W., Dower, W.J., Fodor, S.P.A., Gallop, M.A., (1994) J. Med. Chem., 37, pp. 1385-1401
[8] Zhong, H.M., Greco, M.N., Maryanoff, B.E., J. Org. Chem., , in press
[9] Randolph, J.T., McClure, K.F., Danishefsky, S.J., (1995) J. Am. Chem. Soc., 117, pp. 5712-5719
[10] Thompson, L.A., Ellman, J.A., (1994) Tetrahedron Lett., 35, pp. 9333-9336

← 1 2 3 →