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23 Sep 08:08

Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters

by Luis M. Mori-Quiroz, Kirk W. Shimkin, Sina Rezazadeh, Ryan A. Kozlowski, Donald A. Watson

Abstract

The oxidative copper-catalyzed cross-coupling of functionalized alkyl boronic esters with primary amides is reported. Through the identification of appropriate diketimine ligands, conditions for efficient coupling of both primary and secondary alkyl boronic esters with diverse primary amides, including acetamide, have been developed.

Thumbnail image of graphical abstract

NacNac time! The oxidative copper-catalyzed cross-coupling of functionalized alkyl boronic esters with primary amides is reported. Through the identification of appropriate diketimine ligands, conditions for efficient coupling of both primary and secondary alkyl boronic esters with diverse primary amides, including acetamide, have been developed (see scheme).

15 Sep 13:59

Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres

Chem. Sci., 2016, Advance Article
DOI: 10.1039/C6SC03036J, Edge Article
Open Access Open Access
Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Zackaria Nairoukh, Gunda G. K. S. Narayana Kumar, Yury Minko, Ilan Marek
A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the enantiomerically pure quaternary carbon stereocentre in the [small alpha]-position to the carbonyl group.
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06 Sep 21:26

Enantioselective Synthesis of Di- and Tri-Arylated All-Carbon Quaternary Stereocenters via Copper-Catalyzed Allylic Arylations with Organolithium Compounds

by Sureshbabu Guduguntla, Jean-Baptiste Gualtierotti, Shermin S. Goh and Ben L. Feringa

TOC Graphic

ACS Catalysis
DOI: 10.1021/acscatal.6b01681