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Chiral Lewis acids (CLAs) are a type of Lewis acid catalyst. These acids affect the chirality of the substrate as they react with it. In such reactions, synthesis favors the formation of a specific enantiomer or diastereomer. The method is an enantioselective asymmetric synthesis reaction. Since they affect chirality, they produce optically active products from optically inactive or mixed starting materials. This type of preferential formation of one enantiomer or diastereomer over the other is formally known as asymmetric induction. In this kind of Lewis acid, the electron-accepting atom is typically a metal, such as indium, zinc, lithium, aluminium, titanium, or boron. The chiral-altering ligands employed for synthesizing these acids often have multiple Lewis basic sites (often a diol or a dinitrogen structure) that allow the formation of a ring structure involving the metal atom.[1][2]
Achiral Lewis acids have been used for decades to promote the synthesis of racemic mixtures in myriad different reactions. Since the 1960s, chemists have used Chiral Lewis acids to induce enantioselective reactions. This is useful when the desired product is a specific enantiomer, as is common in drug synthesis. Common reaction types include Diels–Alder reactions, the ene reaction, [2+2] cycloaddition reactions, hydrocyanation of aldehydes, and most notably, Sharpless epoxidations.[3]
- ^ Yamamoto, Hisashi (2007). Lewis acid reagents a practical approach. Knovel. ISBN 978-1-60119-442-8. OCLC 315587750.
- ^ Corey, E. J.; Imwinkelried, Rene; Pikul, Stanislaw; Xiang, Yi Bin (July 1989). "Practical enantioselective Diels-Alder and aldol reactions using a new chiral controller system". Journal of the American Chemical Society. 111 (14): 5493–5495. doi:10.1021/ja00196a081. ISSN 0002-7863.
- ^ Narasaka, Koichi (1991). "Chiral Lewis Acids in Catalytic Asymmetric Reactions". Synthesis. 1991 (1): 1–11. doi:10.1055/s-1991-26364. ISSN 0039-7881.