Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis

被引：73

作者：

Kroll, FEK

Morphy, R

Rees, D

Gani, D

机构：

[1] UNIV ST ANDREWS,SCH CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

[2] UNIV ST ANDREWS,CTR BIOMOL SCI,ST ANDREWS KY16 9ST,FIFE,SCOTLAND

[3] ORGANON LABS,DEPT MED CHEM,NEWHOUSE ML1 5SH,LANARK,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 49期

基金：

英国惠康基金;

关键词：

D O I：

10.1016/S0040-4039(97)10291-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New polystyrene-based resins containing benzyl and aryl vinyl sulfone groups are described. The vinyl sulfone group reacts efficiently with 2 degrees amines, via conjugate addition, and the resin-bound 3 degrees amine products can be quaternised through alkylation. Subsequent deamination to give 3 degrees amines and the regenerated vinyl sulfone occurs in moderate to good yield. Both systems can be recycled and show moderate stability to acids and high stability to nucleophiles including Grignard reagents. (C) 1997 Elsevier Science Ltd.

引用

页码：8573 / 8576

页数：4

共 23 条

[1] [Anonymous], ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANIE.199622881
[2] CARBON-CARBON BOND-FORMING METHODS ON SOLID SUPPORT - UTILIZATION OF KENNER SAFETY-CATCH LINKER
BACKES, BJ
ELLMAN, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) : 11171 - 11172
[3] Synthesis of tertiary amines using a polystyrene (REM) resin
Brown, AR
Rees, DC
Rankovic, Z
Morphy, JR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) : 3288 - 3295
[4] CHEMRA B, 1995, J AM CHEM SOC, V117, P11999
[5] A new cleavage strategy for the solid-phase synthesis of secondary amines
Conti, P
Demont, D
Cals, J
Ottenheijm, HCJ
Leysen, D
[J]. TETRAHEDRON LETTERS, 1997, 38 (16) : 2915 - 2918
[6] LINKERS FOR COMBINATORIAL CHEMISTRY AND REACTION ANALYSIS USING SOLID-PHASE IN-SITU MASS-SPECTROMETRY
EGNER, BJ
CARDNO, M
BRADLEY, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) : 2163 - 2164
[7] RECURSIVE DECONVOLUTION OF COMBINATORIAL CHEMICAL LIBRARIES
ERB, E
JANDA, KD
BRENNER, S
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (24) : 11422 - 11426
[8] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .1. BACKGROUND AND PEPTIDE COMBINATORIAL LIBRARIES
GALLOP, MA
BARRETT, RW
DOWER, WJ
FODOR, SPA
GORDON, EM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (09) : 1233 - 1251
[9] APPLICATIONS OF COMBINATORIAL TECHNOLOGIES TO DRUG DISCOVERY .2. COMBINATORIAL ORGANIC-SYNTHESIS, LIBRARY SCREENING STRATEGIES, AND FUTURE-DIRECTIONS
GORDON, EM
BARRETT, RW
DOWER, WJ
FODOR, SPA
GALLOP, MA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (10) : 1385 - 1401
[10] Preparation of N-substituted aspartic acids via enantiospecific conjugate addition of N-nucleophiles to fumaric acids using methylaspartase: Synthetic utility and mechanistic implications
Gulzar, MS
Akhtar, M
Gani, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (05): : 649 - 655

← 1 2 3 →