Work

Iridium‐Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride

Year: 2016

Type: article

Abstract: The development of the first enantio-, diastereo-, and regioselective iridium-catalyzed allylic alkylation reaction of prochiral enolates to form an all-carbon quaternary stereogenic center with an aliphatic-substituted allylic electrophile is disclosed. The reaction proceeds with good to excellent selectivity with a range of substituted tetralone-derived nucleophiles furnishing products bearing a newly formed vicinal tertiary and all-carbon quaternary stereodyad. The utility of this protocol is further demonstrated via a number of synthetically diverse product transformations.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201609960

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

Funder: National Institute of General Medical Sciences

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