Direct determination of absolute configuration of monoalcohols by bis(magnesium porphyrin)

被引：60

作者：

Lintuluoto, JM ^{[1
]}

Borovkov, VV ^{[1
]}

Inoue, Y ^{[1
]}

机构：

[1] JST, ICORP, Entropy Control Project, Toyonaka, Osaka 5600085, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 46期

关键词：

D O I：

10.1021/ja0267270

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ethane bridged bis(Mg porphyrin) has been found to be an effective sensor for the direct determination of the absolute configuration of a variety of monoalcohols at millimolar concentrations and room temperature based on the CD exciton chirality method. Examination of a variety of synthetic and natural monoalcohols, including α-substituted aliphatic and aromatic alkanols with one chiral center, as well as alicyclic alcohols with 2-5 chiral centers, gave consistent results. In the case of alcohols with multiple chiral centers, the absolute configuration of the carbon α to OH is always read out. Copyright © 2002 American Chemical Society.

引用

页码：13676 / 13677

页数：2

共 19 条

[1] Supramolecular chirogenesis in bis(zinc porphyrin): An absolute configuration probe highly sensitive to guest structure [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

ORGANIC LETTERS, 2000, 2 (11) :1565-1568

[2] Syn-anti conformational changes in zinc porphyrin dimers induced by temperature-controlled alcohol ligation [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

JOURNAL OF PHYSICAL CHEMISTRY B, 1999, 103 (24) :5151-5156

[3] Supramolecular chirality induction in bis(zinc porphyrin) by amino acid derivatives: Rationalization and applications of the ligand bulkiness effect [J].

Borovkov, VV ;

Yamamoto, N ;

Lintuluoto, JM ;

Tanaka, T ;

Inoue, Y .

CHIRALITY, 2001, 13 (06) :329-335

[4] Temperature effect on supramolecular chirality induction in bis(zinc porphyrin) [J].

Borovkov, VV ;

Lintuluoto, JM ;

Fujiki, M ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4403-4407

[5] Supramolecular chirogenesis in zinc porphyrins: Mechanism, role of guest structure, and application for the absolute configuration determination [J].

Borovkov, VV ;

Lintuluoto, JM ;

Inoue, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :2979-2989

[6]

HARADA N, 1983, CIRCULAR DICHROISM E

[7]

Huang XF, 2000, CHEM-EUR J, V6, P216, DOI 10.1002/(SICI)1521-3765(20000117)6:2<216::AID-CHEM216>3.0.CO

[8]

2-1

[9] Zinc porphyrin tweezer in host-guest complexation: Determination of absolute configurations of diamines, amino acids, and amino alcohols by circular dichroism [J].

Huang, XF ;

Rickman, BH ;

Borhan, B ;

Berova, N ;

Nakanishi, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :6185-6186

[10] Chiral recognition by CD-sensitive dimeric zinc porphyrin host.: 1.: Chiroptical protocol for absolute configurational assignments of monoalcohols and primary monoamines [J].

Kurtán, T ;

Nesnas, N ;

Li, YQ ;

Huang, XF ;

Nakanishi, K ;

Berova, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (25) :5962-5973

← 1 2 →