Enantio-differentiation of molecules with diverse functionalities using a single probe

被引：31

作者：

Lakshmipriya, A. ^{[1
,2
]}

Chaudhari, Sachin R. ^{[1
]}

Suryaprakash, N. ^{[1
,2
]}

机构：

[1] NMR Res Ctr, Bangalore 560012, Karnataka, India

[2] Indian Inst Sci, Solid State & Struct Chem Unit, Bangalore 560012, Karnataka, India

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 70期

关键词：

CHIRAL SHIFT-REAGENT; AMINO-ACIDS; ENANTIOSELECTIVE OXIDATION; ABSOLUTE-CONFIGURATION; CARBOXYLIC-ACIDS; DISCRIMINATION; ASSIGNMENT; COMPLEX; ENANTIODIFFERENTIATION; RECOGNITION;

D O I：

10.1039/c5cc05290d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This study reports (1S,2S)-N,N'-dihydroxy-N,N'-bis(diphenylacetyl)-1,2-cyclohexanediamine, a C-2 symmetric chiral hydroxamic acid ((S)-CBHA-DPA), as a unique probe for discrimination of molecules with diverse functionalities. The proposed CSA is also utilized for the accurate measurement of enantiomeric excess.

引用

页码：13492 / 13495

页数：4

共 44 条

[1] Pure Shift 1H NMR: A Resolution of the Resolution Problem? [J].

Aguilar, Juan A. ;

Faulkner, Stephen ;

Nilsson, Mathias ;

Morris, Gareth A. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (23) :3901-3903

[2] Enantioselective oxidation of olefins catalyzed by a chiral bishydroxamic acid complex of molybdenum [J].

Barlan, Allan U. ;

Basak, Arindrajit ;

Yamamoto, Hisashi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (35) :5849-5852

[3] Catalytic enantioselective oxidation of sulfides and disulfides by a chiral complex of bis-hydroxamic acid and molybdenum [J].

Basak, A ;

Barlan, AU ;

Yamamoto, H .

TETRAHEDRON-ASYMMETRY, 2006, 17 (04) :508-511

[4] Highly Effective Configurational Assignment Using Bisthioureas as Chiral Solvating Agents in the Presence of DABCO [J].

Bian, Guangling ;

Fan, Hongjun ;

Huang, Huayin ;

Yang, Shiwei ;

Zong, Hua ;

Song, Ling ;

Yang, Genjin .

ORGANIC LETTERS, 2015, 17 (06) :1369-1372

[5] Quantification of a CH-π Interaction Responsible for Chiral Discrimination and Evaluation of Its Contribution to Enantioselectivity [J].

Carrillo, Romen ;

Lopez-Rodriguez, Matias ;

Martin, Victor S. ;

Martin, Tomas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (42) :7803-7808

[6] Enantiodifferentiation through Frequency- Selective PureShift 1H Nuclear Magnetic Resonance Spectroscopy [J].

Castanar, Laura ;

Perez-Trujillo, Miriam ;

Nolis, Pau ;

Monteagudo, Eva ;

Virgili, Albert ;

Parella, Teodor .

CHEMPHYSCHEM, 2014, 15 (05) :854-857

[7] Ternary ion-pair complexation: a protocol for chiral discrimination and the assignment of absolute configuration of chiral hydroxy acids [J].

Chaudhari, Sachin R. ;

Suryaprakash, N. .

NEW JOURNAL OF CHEMISTRY, 2013, 37 (12) :4025-4030

[8] Simple and efficient methods for discrimination of chiral diacids and chiral alpha-methyl amines [J].

Chaudhari, Sachin R. ;

Suryaprakash, N. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (31) :6410-6419

[9] Three-Component Chiral Derivatizing Protocols for NMR Spectroscopic Enantiodiscrimination of Hydroxy Acids and Primary Amines [J].

Chaudhari, Sachin Rama ;

Suryaprakash, N. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01) :648-651

[10] Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding [J].

Chin, J ;

Kim, DC ;

Kim, HJ ;

Panosyan, FB ;

Kim, KM .

ORGANIC LETTERS, 2004, 6 (15) :2591-2593

← 1 2 3 4 5 →