Work

Iridium-Catalyzed Diastereo-, Enantio-, and Regioselective Allylic Alkylation with Prochiral Enolates

Year: 2016

Type: editorial

Abstract: Transition-metal-catalyzed asymmetric allylic alkylation of \nenolates is a powerful method for the formation of carbon− \ncarbon bonds. Within this field, palladium-catalyzed allylic \nalkylation reactions have undoubtedly been the most studied. \nAside from limited cases, palladium catalysts preferentially \nform the linear substitution product through alkylation at the \nless-substituted terminus of the allylic electrophile (Scheme 1). \nHowever, in contrast to palladium, most other transition metals \n(e.g., Mo, W, Fe, Ru, Co, Rh, Ni, Pt, and Ir) have been shown \nto favor the construction of the branched product, with iridium \ncatalysts being some of the most efficient and selective. The \npotential application of these chiral, branched products to the \nsynthesis of natural products and biologically active compounds \nhas motivated the development of practical and reliable \ntransition-metal-catalyzed methods for their construction.

Source: ACS Catalysis

DOI: 10.1021/acscatal.6b01886

Authors: J. Caleb Hethcox, Samantha E. Shockley, Brian M. Stoltz

Institution: California Institute of Technology

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Camille and Henry Dreyfus Foundation, California Institute of Technology, National Institute of General Medical Sciences

Awards: The Synthesis of Bioactive Polycyclic Natural Products, Total Synthesis of Isopalhinine A

OpenAlex ID: W2518500138

Cites: 34

Cited by: 201

Related to: 10