Quasienantiomers and quasiracemates: new tools for identification, analysis, separation, and synthesis of enantiomers
- PMID: 15915521
- DOI: 10.1002/chem.200500076
Quasienantiomers and quasiracemates: new tools for identification, analysis, separation, and synthesis of enantiomers
Abstract
The old adage "never mix pure organic compounds" holds in spades for enantiomers. After going to all the trouble to make enantiopure molecules, who in their right mind would ever mix them to make a racemate? Quasienantiomers are almost enantiomers, but not quite. Yet unlike enantiomers, the interest is not so much in separating them but in mixing them to make quasiracemates. This backwards thinking opens new possibilities for identification, analysis, separation and synthesis of enantiomers. A short history is provided, the terms are defined and illustrated, and recent applications of quasienantiomers, quasiracemates and related species are reviewed.
Similar articles
-
[Chiral switch: pure enantiomers of drugs instead of racemic mixtures].Ceska Slov Farm. 2004 Nov;53(6):285-93. Ceska Slov Farm. 2004. PMID: 15630994 Czech.
-
Asymmetric syntheses and transformations--tools for chirality multiplication in drug synthesis.Acta Pol Pharm. 2006 Sep-Oct;63(5):333-51. Acta Pol Pharm. 2006. PMID: 17357583 Review.
-
Biotechnological production of enantiopure epoxides by enzymatic kinetic resolution.Appl Microbiol Biotechnol. 2009 Aug;84(2):239-47. doi: 10.1007/s00253-009-2110-9. Epub 2009 Jul 10. Appl Microbiol Biotechnol. 2009. PMID: 19590868 Review.
-
Concise synthesis of enantiopure alpha-trifluoromethyl alanines, diamines, and amino alcohols via the Strecker-type reaction.J Org Chem. 2006 Sep 1;71(18):7075-8. doi: 10.1021/jo0607717. J Org Chem. 2006. PMID: 16930068
-
Quasiracemic synthesis: concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine.J Am Chem Soc. 2002 May 22;124(20):5774-81. doi: 10.1021/ja025606x. J Am Chem Soc. 2002. PMID: 12010052
Cited by
-
Fluorous Mixture Synthesis of Four Stereoisomers of the C21-C40 Fragment of Tetrafibricin.Synlett. 2010 Mar 1;2010(4):667-674. doi: 10.1055/s-0029-1219376. Synlett. 2010. PMID: 20686632 Free PMC article.
-
Fluorous mixture synthesis of two libraries with hydantoin-, and benzodiazepinedione-fused heterocyclic scaffolds.J Comb Chem. 2006 Sep-Oct;8(5):687-95. doi: 10.1021/cc060061e. J Comb Chem. 2006. PMID: 16961407 Free PMC article.
-
Catalytic parallel kinetic resolution under homogeneous conditions.J Org Chem. 2010 Jul 16;75(14):4674-85. doi: 10.1021/jo100695z. J Org Chem. 2010. PMID: 20557113 Free PMC article.
-
Selective control of reconfigurable chiral plasmonic metamolecules.Sci Adv. 2017 Apr 21;3(4):e1602803. doi: 10.1126/sciadv.1602803. eCollection 2017 Apr. Sci Adv. 2017. PMID: 28439556 Free PMC article.
-
A "shortcut" Mosher ester method to assign configurations of stereocenters in nearly symmetric environments. Fluorous mixture synthesis and structure assignment of petrocortyne A.J Am Chem Soc. 2009 Apr 22;131(15):5411-3. doi: 10.1021/ja900849f. J Am Chem Soc. 2009. PMID: 19323551 Free PMC article.
Publication types
MeSH terms
LinkOut - more resources
Full Text Sources