Chemical reaction(s) which favor one chiral isomer over another
In the Sharpless dihydroxylation reaction the chirality of the product can be controlled by the "AD-mix" used. This is an example of enantioselective synthesis using asymmetric induction
Key: RL = Largest substituent; RM = Medium-sized substituent; RS = Smallest substituentTwo enantiomers of a generic alpha amino acid
Carbon at the chiral center
Carboxylic acid group
R group
Hydrogen
Enantioselective synthesis, also called asymmetric synthesis,[1] is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts."[2]
Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers.
Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity.
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "asymmetric synthesis". doi:10.1351/goldbook.A00484
^IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "stereoselective synthesis". doi:10.1351/goldbook.S05990
and 26 Related for: Enantioselective synthesis information
Enantioselectivesynthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction...
since this was the first total synthesis of (±)-totarol, it is notable. The first total enantioselectivesynthesis of totarol was achieved in 1979 (Scheme...
ISBN 978-0-19-850346-0. Tiano, Martin (2020). "Enantioselective Michael Addition: An Experimental Introduction to Asymmetric Synthesis". Journal of Chemical Education...
L. (2002-07-01). "Strained Silacycles in Organic Synthesis: A New Reagent for the Enantioselective Allylation of Aldehydes". Journal of the American...
PMID 12381175. S2CID 32048193. Trost BM, Tang W (December 2002). "Enantioselectivesynthesis of (-)-codeine and (-)-morphine". Journal of the American Chemical...
exo products. This selectivity can be tuned using metal catalysis. Enantioselective cycloaddition of azomethine ylides using chiral catalysts was first...
are widely used for enantioselectivesynthesis. They are widely used in asymmetric catalysis. Modern enantioselectivesynthesis typically applies a well-chosen...
Reported in 1993 by Nicos Petasis as a practical method towards the synthesis of a geometrically pure antifungal agent, naftifine. In the Petasis reaction...
2016, Burns and co-workers at Stanford University reported an enantioselectivesynthesis of both the [3]- and [5]-ladderane lipid tails and their incorporation...
group reported a copper-catalyzed enantioselective hydroalkylation of bromide tethered styrenyl-type olefins. The synthesis of a variety of 4-, 5-, and 6-membered...
effective for enantioselectivesynthesis, achieving a modest 15% enantiomeric excess. Knowles was also the first to apply enantioselective metal catalysis...
PMID 12381175. S2CID 32048193. Trost BM, Tang W (December 2002). "Enantioselectivesynthesis of (-)-codeine and (-)-morphine". Journal of the American Chemical...
AG and Hoffmann-La Roche. Proline's chiral structure enables enantioselectivesynthesis, favoring a particular enantiomer or diastereomer.: 5574 : 47 ...
Olivier (2006). "Biaryl Axis as a Stereochemical Relay for the EnantioselectiveSynthesis of Antimicrotubule Agents". Angewandte Chemie International Edition...
Corey of Harvard University presented the enantioselectivesynthesis of Aflatoxin B2. The total synthesis of Aflatoxin B2 is a multistep sequence that...
intramolecular Robinson annulation to provide a straightforward enantioselectivesynthesis of tetracyclic core of platensimycin. The key Robinson annulation...
the 15-membered ring via ring-closing metathesis: A more recent enantioselectivesynthesis involves an intramolecular aldol addition/dehydration reaction...
1039/CT9171100762. Corey EJ, Luo G, Lin LS (1997). "A simple enantioselectivesynthesis of the biologically active tetracyclic marine sesterterpene scalarenedial"...
pp. 89–114. ISBN 9783527605767. Jaeger KE, Eggert T (August 2004). "Enantioselective biocatalysis optimized by directed evolution". Current Opinion in Biotechnology...
1021/jo00318a010. hdl:2268/237697. Davies HM, Huby NJ (1992). "Enantioselectivesynthesis of tropanes by reaction of rhodium-stabilized vinylcarbenoids...
The Sharpless epoxidation reaction is an enantioselective chemical reaction to prepare 2,3-epoxyalcohols from primary and secondary allylic alcohols. The...
usually the result of enzymatic modification after translation (protein synthesis). For example, phosphorylation of serine by kinases and dephosphorylation...
sulfinamides, this class of compounds is used as catalysts in enantioselectivesynthesis. Sulfonamide (medicine) Sulfamic acid Sulfamide Actor, P.; Chow...
In 1828, Friedrich Wöhler published a paper on his serendipitous urea synthesis from potassium cyanate and ammonium sulfate; some regarded that as a direct...
glucose to pyruvate by cellular respiration); or anabolic—the building up (synthesis) of compounds (such as proteins, carbohydrates, lipids, and nucleic acids)...
with the Shi epoxidation, these reactions are useful for the enantioselectivesynthesis of chiral epoxides. Oxaziridine reagents may also be used to generate...
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