Organic Chemistry And Reaction Mechanisms Codexery

Enantioselective synthesis

Chemical synthesis favoring one enantiomer over another.

Last updated

Enantioselective synthesis is a form of chemical synthesis that produces stereoisomeric products in unequal amounts, as defined by IUPAC.[1] It is important because biological systems often react differently with each enantiomer of a compound.[2]

Last updated 2026-10-05 from the source article.

Quick Facts

Field
Chemistry
Known for
Asymmetric synthesis favoring one enantiomer or diastereomer
Key concept
  • Asymmetric induction via chiral features in substrate
  • reagent
  • catalyst
  • or environment

Facts from the source article.

Key facts and history

Louis Pasteur proposed in 1848 that this property had a molecular basis originating from dissymmetry.[3] Hermann Emil Fischer outlined the concept of asymmetric induction in 1894.[4] Fischer also performed what is now regarded as the first example of enantioselective synthesis by elongating sugars.[5] The first enantioselective chemical synthesis is most often attributed to Willy Marckwald in 1904 for a brucine-catalyzed decarboxylation.[6]

Knowles developed an enantioselective hydrogenation step for the industrial production of L-DOPA while at the Monsanto Company.[7] In 1874, Jacobus Henricus van 't Hoff and Joseph Le Bel each put forward the idea that carbon has a tetrahedral geometry.[3] William S. Knowles, Ryōji Noyori, and K. Barry Sharpless were the pioneers of metal-catalysed enantioselective synthesis, and they were awarded the 2001 Nobel Prize in Chemistry for this work.[7] E.J. Corey first introduced the concept of chiral auxiliaries in 1978.[8]

References

  1. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0) en.wikipedia.org
  2. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: Gal, "The Discovery of Stereoselectivity at Biological Receptors: Arnaldo Piutti and the Taste of the Asparagine Enantiomers-History and Analysis on the 125th Anniversary", Chirality, 2012, p. 959–976; "Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones", J. Agric. Food Chem., 1971, p. 785–787 (we also read that source) en.wikipedia.org
  3. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: "Selected Papers on Natural Optical Activity (SPIE Milestone Volume 15)", SPIE, 1990; Gal, "Louis Pasteur, language, and molecular chirality. I. Background and Dissymmetry", Chirality, January 2011, p. 1–16; Pasteur, L., "Researches on the molecular asymmetry of natural organic products, English translation of French original, published by Alembic Club Reprints (Vol. 14, pp. 1–46) in 1905, facsimile reproduction by SPIE in a; Pedro Cintas, "Tracing the Origins and Evolution of Chirality and Handedness in Chemical Language", A en.wikipedia.org
  4. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: Fischer, "Synthesen in der Zuckergruppe II", Berichte der Deutschen Chemischen Gesellschaft, 1 October 1894, p. 3189–3232 (original not read by us) en.wikipedia.org
  5. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: Fischer, "Ueber Mannose. II", Berichte der Deutschen Chemischen Gesellschaft, 1 January 1889, p. 365–376 (original not read by us) en.wikipedia.org
  6. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: Koskinen, "Asymmetric synthesis of natural products", Wiley, 2013, p. 17, 28–29; Marckwald, W., "Ueber asymmetrische Synthese", Berichte der Deutschen Chemischen Gesellschaft, 1904, p. 349–354; Campbell, "Biosynthesis of lovastatin and related metabolites formed by fungal iterative PKS enzymes", Biopolymers, 23 June 2010, p. 755–763; Koskinen, "Asymmetric synthesis of natural products", Wiley, 2013, p. 17, 28–29 (we also read that source) en.wikipedia.org
  7. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: Vineyard, "Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst", Journal of the American Chemical Society, 1977, p. 5946–5952; Knowles, "Asymmetric Hydrogenations (Nobel Lecture)", Angewandte Chemie International Edition, 2002, p. 1999–2007; Knowles, "Application of organometallic catalysis to the commercial production of L-DOPA", Journal of Chemical Education, March 1986, p. 222 (we also read that source) en.wikipedia.org
  8. Wikipedia, "Enantioselective synthesis" (CC BY-SA 4.0), which cites: Ensley, "Convenient synthesis of a highly efficient and recyclable chiral director for asymmetric induction", The Journal of Organic Chemistry, 1978, p. 1610–1612 (original not read by us) en.wikipedia.org

Each numbered sentence above was checked against the source it cites before publication. Sentences citing Wikipedia adapt text from the English Wikipedia article Enantioselective synthesis (contributors), used under CC BY-SA 4.0; this entry is available under the same licence. Other sources were used for facts only; no text or images are copied from them.

Related entries

Named in this entry

Diastereomer

More in Organic Chemistry And Reaction Mechanisms

E–Z notationFree-radical additionGrignard reactionHaloform reactionHammond's postulateArrow pushingAtropisomerCahn–Ingold–Prelog priority rulesChirality (chemistry)Cis–trans isomerismConvergent synthesisCycloaddition

Sources

Compiled from Wikipedia and the sources listed below. Text from Wikipedia is available under CC BY-SA 4.0; this entry is adapted from it.

Spotted an error? Know more?

Reader corrections go straight into our review queue. Suggest an edit · How this site is sourced

Comments

Loading…
Open in the interactive codex →