Emergence of a single solid chiral state from a nearly racemic amino acid derivative

被引：376

作者：

Noorduin, Wim L. ^{[2
]}

Izumi, Toshiko ^{[3
,4
]}

Millemaggi, Alessia ^{[5
]}

Leeman, Michel ^{[1
]}

Meekes, Hugo ^{[2
]}

Van Enckevort, Willem J. P. ^{[2
]}

Kellogg, Richard M. ^{[1
]}

Kaptein, Bernard ^{[5
]}

Vlieg, Elias ^{[2
]}

Blackmond, Donna G. ^{[3
,4
]}

机构：

[1] Syncom BV, NL-9747 AT Groningen, Netherlands

[2] Radbound Univ Nijmegen, IMM Solid State Chem, NL-6525 ED Nijmegen, Netherlands

[3] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[4] Univ London Imperial Coll Sci Technol & Med, Dept Chem Engn, London SW7 2AZ, England

[5] DSM Pharmaceut Prod Adv Synth Catalysis & Dev, NL-6160 MD Geleen, Netherlands

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 04期

关键词：

D O I：

10.1021/ja7106349

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The evolution of a single chiral solid state is reported for an amino acid derivative starting from a nearly racemic mixture of solid left- and right-handed crystals. Attrition-enhanced dissolution and recrystallization processes based on solubility considerations of the Gibbs-Thomson rule, coupled with solution-phase racemization, drive this near-equilibrium system inexorably to single chirality in the solid phase.

引用

页码：1158 / +

页数：3

共 35 条

[1] RESOLUTION OF CONGLOMERATES BY STEREOSELECTIVE HABIT MODIFICATIONS [J].

ADDADI, L ;

BERKOVITCHYELLIN, Z ;

DOMB, N ;

GATI, E ;

LAHAV, M ;

LEISEROWITZ, L .

NATURE, 1982, 296 (5852) :21-26

[2] RESOLUTION OF CONGLOMERATES WITH THE ASSISTANCE OF TAILOR-MADE IMPURITIES - GENERALITY AND MECHANISTIC ASPECTS OF THE RULE OF REVERSAL - A NEW METHOD FOR ASSIGNMENT OF ABSOLUTE-CONFIGURATION [J].

ADDADI, L ;

WEINSTEIN, S ;

GATI, E ;

WEISSBUCH, I ;

LAHAV, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4610-4617

[3]

Armstrong DW, 2001, CHIRALITY, V13, P153, DOI 10.1002/1520-636X(2001)13:3<153::AID-CHIR1013>3.0.CO

[4]

2-8

[5] PHENOL OXIDATION AND BIOSYNTHESIS .5. SYNTHESIS OF GALANTHAMINE [J].

BARTON, DHR ;

KIRBY, GW .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAR) :806-&

[6] Response to "Comments on a possible transition to solid-phase homochirality" [J].

Blackmond, Donna G. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (36) :10306-10311

[7] Chiral amnesia as a driving force for solid-phase homochirality [J].

Blackmond, Donna G. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (12) :3290-3295

[8] ENANTIOSELECTIVE AUTOCATALYSIS - SPONTANEOUS RESOLUTION AND THE PREBIOTIC GENERATION OF CHIRALITY [J].

BONNER, WA .

ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE, 1994, 24 (01) :63-78

[9] Crystallization-induced diastereomer transformations [J].

Brands, Karel M. J. ;

Davies, Antony J. .

CHEMICAL REVIEWS, 2006, 106 (07) :2711-2733

[10]

Calvin M, 1969, MOL EVOLUTION

← 1 2 3 4 →