Work

Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents

Year: 2017

Type: article

Abstract: The first enantioselective iridium-catalyzed allylic alkylation reaction of a masked acyl cyanide (MAC) reagent has been developed. The transformation allows for the use of an umpoled synthon, which serves as a carbon monoxide equivalent. The reaction proceeds with good yield and excellent selectivity up to gram scale for a wide range of substituted allylic electrophiles, delivering products amenable to the synthesis of highly desirable, enantioenriched vinylated α-aryl carbonyl derivatives.

Source: Organic Letters

DOI: 10.1021/acs.orglett.7b00449

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: green

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