A chemoselective rhodium(II) mediated solid phase 1,3-dipolar cycloaddition and its application to a thermally self-cleaving furan scaffold

被引：46

作者：

Whitehouse, DL ^{[1
]}

Nelson, KH ^{[1
]}

Savinov, SN ^{[1
]}

Austin, DJ ^{[1
]}

机构：

[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06520

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(97)01768-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoselective rhodium(II) mediated 1,3-dipolar cycloaddition reaction on solid-phase for the construction of a template-directed scaffold is described. In this paper, the reaction of acetylenes with isomunchnones is presented as a general methodology for the combinatorial formation of a furan based library. Additionally, through the development of a novel thermolytic cleavage step, this furan synthesis yields pure product from the solid-phase in a temperature dependent manner. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：7139 / 7142

页数：4

相关论文

共 12 条

[1] A NOVEL PROCEDURE FOR THE SYNTHESIS OF LIBRARIES CONTAINING SMALL ORGANIC-MOLECULES [J].

CARELL, T ;

WINTNER, EA ;

BASHIRHASHEMI, A ;

REBEK, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (20) :2059-2061

[2] Solid-phase synthesis of proline analogs via a three component 1,3-dipolar cycloaddition [J].

Hamper, BC ;

Dukesherer, DR ;

South, MS .

TETRAHEDRON LETTERS, 1996, 37 (21) :3671-3674

[3] Stereoselective synthesis of highly functionalised pyrrolidines via 1,3-dipolar cycloaddition reactions on a solid support. [J].

Hollinshead, SP .

TETRAHEDRON LETTERS, 1996, 37 (51) :9157-9160

[4] Dipolar cycloadditions in solid-phase organic synthesis (SPOS) [J].

Kantorowski, EJ ;

Kurth, MJ .

MOLECULAR DIVERSITY, 1997, 2 (04) :207-216

[5] Solid-phase combinatorial synthesis of polyisoxazolines: A two-reaction iterative protocol [J].

Kurth, MJ ;

Randall, LAA ;

Takenouchi, K .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8755-8761

[6] Glycosamino acids: New building blocks for combinatorial synthesis [J].

McDevitt, JP ;

Lansbury, PT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (16) :3818-3828

[7] COMBINATORIAL ORGANIC-SYNTHESIS OF HIGHLY FUNCTIONALIZED PYRROLIDINES - IDENTIFICATION OF A POTENT ANGIOTENSIN-CONVERTING ENZYME-INHIBITOR FROM A MERCAPTOACYL PROLINE LIBRARY [J].

MURPHY, MM ;

SCHULLEK, JR ;

GORDON, EM ;

GALLOP, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (26) :7029-7030

[8]

OSTERHOUT MH, 1994, SYNTHESIS-STUTTGART, P123

[9]

PADWA A, 1994, ANGEW CHEM INT EDIT, V33, P1797, DOI 10.1002/anie.199417971

[10] Ligand-dependent site selectivity in the Rh(II)-catalyzed decomposition of a glycine-derived diazo acetoacetamide [J].

Prein, M ;

Padwa, A .

TETRAHEDRON LETTERS, 1996, 37 (39) :6981-6984