Related Experiment Video
Updated: Jun 26, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Recent development and improvement for boron hydride-based catalytic asymmetric reduction of unsymmetrical ketones
1Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon, Kangwondo, 200-702, Republic of Korea. btcho@hallym.ac.kr
Abstract:
Catalytic asymmetric reduction of prochiral ketones with hydrides such as boranes and borohydrides is one of the simplest and the most convenient methods for obtaining chiral alcohols. This tutorial review describes the most significant advances recently achieved for enhancing the enantioselectivity and practicability of the reduction using this methodology. The review covers the development of new homogeneous and/or immobilized catalysts for asymmetric reduction using borane or borohydride reagents and practical improvement of the well-known oxazaborolidine (OAB)-catalysed reduction through developing more stable, cost effective and recoverable OABs, scalable and environmental friendly borane sources, and one-pot procedures for the reduction.
Related Concept Videos
Alcohols from Carbonyl Compounds: Reduction
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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...
Hydroboration-Oxidation of Alkenes
Carboxylic Acids to Primary Alcohols: Hydride Reduction
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.

