Novel C3v-Symmetric tripodal scaffold, triethyl cis,cis,cis-2,5,8-tribenzyltrindane-2,5,8-tricarboxylate, for the construction of artificial receptors

被引：53

作者：

Choi, HJ ^{[1
]}

Park, YS

Yun, SH

Kim, HS

Cho, CS

Ko, K

Ahn, KH

机构：

[1] Kyungpook Natl Univ, Dept Ind Chem, Taegu 702701, South Korea

[2] Kyungpook Natl Univ, Dept Chem Engn, Taegu 702701, South Korea

[3] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 05期

关键词：

D O I：

10.1021/ol017294t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A novel C-3nu-symmetric scaffold, trindane 7, has been efficiently synthesized from 1, 3,5-tris(bromomethyl)-2,4,6-tris(chloromethyl)benzene (1) in six steps with 47% overall yield. The control of all-synstereochemistry in the tribenzylation step has been achieved by blocking one side of the trindane ring as metal carbonyl complexes. The potential utility of trindane 7 as a receptor skeleton has been examined with a urea derivative 12 toward several anionic guests.

引用

收藏

页码：795 / 798

页数：4

相关论文

共 41 条

[21] Synthesis and characterisation of novel ruthenium(II) bipyridyl and ferrocenoyl cavitand receptors for the recognition of anionic guests [J].

Dumazet, I ;

Beer, PD .

TETRAHEDRON LETTERS, 1999, 40 (04) :785-788

[22] Anion receptor chemistry: highlights from 1999 [J].

Gale, PA .

COORDINATION CHEMISTRY REVIEWS, 2001, 213 :79-128

[23] EFFICIENT COUPLING OF AMINO-ACID DERIVATIVES TO RIGID ORGANIC SCAFFOLDS - MODEL SYNTHESES FOR DE-NOVO PROTEINS [J].

GIBB, BC ;

MEZO, AR ;

CAUSTON, AS ;

FRASER, JR ;

TSAI, FCS ;

SHERMAN, JC .

TETRAHEDRON, 1995, 51 (32) :8719-8732

[24] Troger's base molecular scaffolds in dicarboxylic acid recognition [J].

Goswami, S ;

Ghosh, K ;

Dasgupta, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) :1907-1914

[25]

Gupta HK, 1997, ORGANOMETALLICS, V16, P4355

[26] Metal complexes of trindane: Possible precursors of sumanene [J].

Gupta, HK ;

Lock, PE ;

McGlinchey, MJ .

ORGANOMETALLICS, 1997, 16 (16) :3628-3634

[27] Solvent and leaving group effects on the mono- vs. dialkylation of alkali salts of diethyl malonate with 1,2-bis-, 1,2,4,5-tetrakis- and 1,2,3,4,5,6-hexakis(halomethyl)benzenes. A new insight into selectivity control of malonester synthesis. [J].

Holy, P ;

Havranek, M ;

Pankova, M ;

Ridvan, L ;

Zavada, J .

TETRAHEDRON, 1997, 53 (24) :8195-8210

[28] EQNMR - A COMPUTER-PROGRAM FOR THE CALCULATION OF STABILITY-CONSTANTS FROM NUCLEAR-MAGNETIC-RESONANCE CHEMICAL-SHIFT DATA [J].

HYNES, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (02) :311-312

[29] REGIOSPECIFIC AND STEREOSPECIFIC FUNCTIONALIZATION OF BENZYLIC SITES BY TRICARBONYLCHROMIUM ARENE COMPLEXATION [J].

JAOUEN, G ;

TOP, S ;

LACONI, A ;

COUTURIER, D ;

BROCARD, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (07) :2207-2208

[30]

Kim SG, 2000, CHEM-EUR J, V6, P3399, DOI 10.1002/1521-3765(20000915)6:18<3399::AID-CHEM3399>3.0.CO

← 1 2 3 4 5 →