A two-step chemical/chiroptical method for determining absolute configurations of α-hydroxy acids

被引：37

作者：

Rickman, BH ^{[1
]}

Matile, S ^{[1
]}

Nakanishi, K ^{[1
]}

Berova, N ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 20期

关键词：

D O I：

10.1016/S0040-4020(98)00221-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, chemical/chiroptical approach based on the CD exciton chirality method has been developed to determine the absolute configuration of a-hydroxy acids. This approach consists of amidation of the carboxyl group with ethanolamine followed by derivatization with the hydrophobic 10,15,20-triphenylporphyrinyl-5-benzoyl chromophore to form pi,pi-bisporphyrin derivatives which undergo intramolecular stacking. The sign of the observed bisignate couplet resulting from this stacking tin methylcyclohexane) is dictated by the preferred lower energy conformer and reflects the absolute configuration of the stereogenic center. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5041 / 5064

页数：24

相关论文

共 33 条

[1] PI-PI AGGREGATION IN METALLOPORPHYRINS - CAUSATIVE FACTORS [J].

ABRAHAM, RJ ;

EIVAZI, F ;

PEARSON, H ;

SMITH, KM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (17) :699-701

[2] NMR-SPECTRA OF PORPHYRINS .15. SELF-AGGREGATION IN ZINC(II) PROTOPORPHYRIN-IX DIMETHYL ESTER [J].

ABRAHAM, RJ ;

FELL, SCM ;

PEARSON, H ;

SMITH, KM .

TETRAHEDRON, 1979, 35 (14) :1759-1766

[3] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES [J].

AKIYAMA, T ;

NISHIMOTO, H ;

OZAKI, S .

TETRAHEDRON LETTERS, 1991, 32 (10) :1335-1338

[4]

[Anonymous], TOTAL SYNTHESIS NATU

[5]

BARTON DHR, 1979, COMPREHENSIVE ORGANI, P69

[6] SYNTHESIS AND SPECTROSCOPIC PROPERTIES OF A NOVEL COFACIAL CHLOROPHYLL-BASED DIMER [J].

BUCKS, RR ;

BOXER, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) :340-343

[7] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

BAKSHI, RK .

TETRAHEDRON LETTERS, 1990, 31 (05) :611-614

[8] A NEW PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-ARYLOXY AND ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

LINK, JO .

TETRAHEDRON LETTERS, 1992, 33 (24) :3431-3434

[9] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[10] ASYMMETRIC OXYGENATION OF CHIRAL IMIDE ENOLATES - A GENERAL-APPROACH TO THE SYNTHESIS OF ENANTIOMERICALLY PURE ALPHA-HYDROXY CARBOXYLIC-ACID SYNTHONS [J].

EVANS, DA ;

MORRISSEY, MM ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (14) :4346-4348

← 1 2 3 4 →