ENANTIOSELECTIVE COMPLEXATION OF ORGANIC AMMONIUM-IONS BY SIMPLE TETRACYCLIC PODAND IONOPHORES

被引：86

作者：

WANG, XH ^{[1
]}

ERICKSON, SD ^{[1
]}

IIMORI, T ^{[1
]}

STILL, WC ^{[1
]}

机构：

[1] COLUMBIA UNIV,DEPT CHEM,NEW YORK,NY 10027

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 11期

关键词：

D O I：

10.1021/ja00037a014

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of enantiomerically pure, C2-symmetric tetracyclic podands are synthesized and studied. These host molecules have methyl substitution, which allows only a few low-energy conformations, and they form well-defined complexes with chiral ammonium salts. With derivatives of alpha-phenethylammonium hexafluorophosphate as guests, binding enantioselectivity ranges from approximately 0 to 60% ee. X-ray structures of several podand/chiral ammonium perchlorate complexes are described along with a conformational analysis of the podands and their complexes.

引用

页码：4128 / 4137

页数：10

共 24 条

[1] CONFORMATIONAL MOBILITY AND OPTICAL ROTATION EFFECTS OF AROMATIC NUCLEI
BREWSTER, JH
BUTA, JG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (10) : 2233 - +
[2] THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES (NOBEL LECTURE)
CRAM, DJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (08): : 1009 - 1020
[3] HOST GUEST COMPLEXATION .29. EXPANDED HEMISPHERANDS
CRAM, DJ
DEGRANDPRE, M
KNOBLER, CB
TRUEBLOOD, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) : 3286 - 3292
[4] COUNTERANION EFFECTS ON COMPLEXATION OF CATIONS
DOXSEE, KM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) : 4712 - 4715
[5] ON THE STEREOCHEMICAL CONTROL OF COMPLEXATION IN TETRAHYDROPYRANOID PODAND IONOPHORES
ERICKSON, SD
STILL, WC
[J]. TETRAHEDRON LETTERS, 1990, 31 (30) : 4253 - 4256
[6] HYDROGEN-BOND DIRECTED COCRYSTALLIZATION AND MOLECULAR RECOGNITION PROPERTIES OF DIARYLUREAS
ETTER, MC
URBANCZYKLIPKOWSKA, Z
ZIAEBRAHIMI, M
PANUNTO, TW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (23) : 8415 - 8426
[7] ENANTIOSELECTIVE COMPLEXATION WITH A CONFORMATIONALLY HOMOGENEOUS C2 PODAND IONOPHORE
IIMORI, T
ERICKSON, SD
RHEINGOLD, AL
STILL, WC
[J]. TETRAHEDRON LETTERS, 1989, 30 (50) : 6947 - 6950
[8] PODAND IONOPHORES - A NEW CLASS OF NONMACROCYCLIC YET PREORGANIZED HOSTS FOR CATIONS
IIMORI, T
STILL, WC
RHEINGOLD, AL
STALEY, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) : 3439 - 3440
[9] SYNTHESIS OF (R)-(+)-H-3-ETOMIDATE
JANSSEN, CGM
THIJSSEN, JBA
VERLUYTEN, WLM
HEYKANTS, JJP
[J]. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1987, 24 (08) : 909 - 918
[10] THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION (INOC) ROUTE TO THE ERGOT ALKALOIDS - USE OF THE ISOXAZOLINE TO GAMMA-AMINO ALCOHOL CONVERSION IN THE TOTAL SYNTHESIS OF (+)-PALICLAVINE
KOZIKOWSKI, AP
CHEN, YY
WANG, BC
XU, ZB
[J]. TETRAHEDRON, 1984, 40 (12) : 2345 - 2358

← 1 2 3 →