Work

Highly Regio- and Enantioselective Vicinal Dihalogenation of Allyl Amides

Year: 2017

Type: article

Abstract: We report a highly regio-, diastereo- and enantioselective vicinal dihalogenation of allyl amides. E- and Z-alkenes with both aryl and alkyl substituents were compatible with this chemistry. This is the result of exquisite catalyst controlled regioselectivity enabling use of electronically unbiased substrates. The reaction employs commercially available catalysts and halenium sources along with cheap inorganic halide salts to affect this transformation. A preliminary effort to extend this chemistry to heterodihalogenation is also presented.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.6b09203

Authors: Bardia Soltanzadeh, Arvind Jaganathan, Yi Yi, Hajoon Yi, Richard J. Staples, Babak Borhan

Institution: Michigan State University

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: G1495357881, Predicted Reaction Discovery and Application of Catalytic Asymmetric Alkene Halogenations