Enantioenrichment by Iterative Retro-Aldol/Aldol Reaction Catalyzed by an Achiral or Racemic Base

被引:50
作者
Flock, Angelika M. [1 ]
Reucher, Christine M. M. [1 ]
Bolm, Carsten [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
关键词
aldol reaction; asymmetric amplification; enantioenrichment; grinding; reversible reactions; CHIRAL-SYMMETRY-BREAKING; ATTRITION-ENHANCED DERACEMIZATION; RESOLUTION; CRYSTALLIZATION; HOMOCHIRALITY; EMERGENCE; STATE;
D O I
10.1002/chem.200903497
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chemical Equation Presented Did nature use the same strategy? The combination of crystal growth and iterative retro-aldol/aldol reactions catalyzed by a simple achiral (or racemic) base allows improvement of the enantiomer ratio of a product obtained from a stereochemically imperfect aldol reaction (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3918 / 3921
页数:4
相关论文
共 43 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]   GROWTH AND DISSOLUTION OF ORGANIC-CRYSTALS WITH TAILOR-MADE INHIBITORS - IMPLICATIONS IN STEREOCHEMISTRY AND MATERIALS SCIENCE [J].
ADDADI, L ;
BERKOVITCHYELLIN, Z ;
WEISSBUCH, I ;
VANMIL, J ;
SHIMON, LJW ;
LAHAV, M ;
LEISEROWITZ, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (06) :466-485
[3]   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
[4]  
ADDADI L, 1985, ANGEW CHEM, V97, P476
[5]   Chiral amnesia as a driving force for solid-phase homochirality [J].
Blackmond, Donna G. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (12) :3290-3295
[6]   Nonlinear effects in proline-catalysed aldol reactions under solvent-free conditions based on the ternary phase behaviour of scalemic proline [J].
Bruckmann, Angelika ;
Rodriguez, Belen ;
Bolm, Carsten .
CRYSTENGCOMM, 2009, 11 (03) :404-407
[7]   OPTICAL RESOLUTION BY DIRECT CRYSTALLIZATION OF ENANTIOMER MIXTURES [J].
COLLET, A ;
BRIENNE, MJ ;
JACQUES, J .
CHEMICAL REVIEWS, 1980, 80 (03) :215-230
[8]   Comments on a possible transition to solid-phase homochirality [J].
Crusats, Joaquim ;
Veintemillas-Verdaguer, Sabino ;
Ribo, Josep M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (36) :10303-10305
[9]   Homochirality as a consequence of thermodynamic equilibrium? [J].
Crusats, Joaquim ;
Veintemillas-Verdaguer, Sabino ;
Ribo, Josep M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) :7776-7781
[10]  
Gibbs J. W., 1948, THERMODYNAMICS COLLE, VI