General Route for Preparing β-Nitrocarbonyl Compounds Using Copper Thermal Redox Catalysis
Author(s) -
Amber A. S. Gietter,
Peter G. Gildner,
Andrew P. Cinderella,
Donald A. Watson
Publication year - 2014
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/ol5014153
Subject(s) - chemistry , functional group , steric effects , catalysis , redox , copper , alkylation , nitro , combinatorial chemistry , organic chemistry , molecule , alkyl , polymer
Using a simple copper catalyst, the alkylation of nitroalkanes with α-bromocarbonyls is now possible. This method provides a general, functional group tolerant route to β-nitrocarbonyl compounds, including nitro amides, esters, ketones, and aldehydes. The highly sterically dense, functional group rich products from these reactions can be readily elaborated into a range of complex nitrogen-containing molecules, including highly substituted β-amino acids.
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