The Zirkonium-catalyzed Asymmetric Carbo-Alumination reaction (or ZACA reaction) was developed by Nobel laureate Ei-ichi Negishi

Ei-ichi Negishi

is a Japanese chemist who has spent most of his career at Purdue University, United States. He is best known for his discovery of the Negishi coupling. He was awarded the 2010 Nobel Prize in Chemistry "for palladium catalyzed cross couplings in organic synthesis" jointly with Richard F. Heck and...

. It facilitates the chiral functionalization of alkenes using organoaluminium compounds under the influence of chiral bis-indenylzirkonium catalysts (e.g. bearing chiral terpene

Terpene

Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...

 residues, as in (+)- or (-)-bis[(1-neomenthyl)indenyl]zirconium dichloride). In a first step the alkene inserts into an Al-C bond of the reagent, forming a new chiral organoaluminum compound in which the aluminium atom occupies the lesser hindered position. This intermediate is usually oxidized by oxygen to form the corresponding chiral alcohol (cf. Hydroboration–oxidation reaction). The reaction can also be applied to dienes, where the least sterically hindered double bond is attacked selectively.