Ru-Catalyzed Asymmetric Hydrogenation of Chiral δ-Hydroxy-β-Keto Acid Derivatives
Limin Xu1, Yuxuan Zhang1, Yan Lu1
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China.
Abstract:
Ru-catalyzed stereoselective asymmetric hydrogenation of multifunctionalized ketones has been a formidable challenge, and few related successful works have been reported. Herein, we report our research on Ru-catalyzed asymmetric hydrogenation of chiral δ-hydroxy-β-keto acid derivatives, which achieves excellent diastereoselectivity (up to >99% de). This procedure provides a new route for the synthesis of pure syn- and anti-3,5-dihydroxy acid derivatives, which serve as key intermediates in natural products and drug molecules, such as statins.
Related Concept Videos
Prochirality
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Radical Anti-Markovnikov Addition to Alkenes: Overview


