1374760-62-9Relevant academic research and scientific papers
Enantioselective synthesis of all-carbon quaternary stereogenic centers via copper-catalyzed asymmetric allylic alkylation of (Z)-allyl bromides with organolithium reagents
Faans-Mastral, Martn,Vitale, Romina,Prez, Manuel,Feringa, Ben L.
supporting information, p. 4209 - 4212 (2015/03/14)
A copper/phosphoramidite catalyzed asymmetric allylic alkylation of Z trisubstituted allyl bromides with organolithium reagents is reported. The reaction affords all-carbon quaternary stereogenic centers in high yields and very good regio- and enantiosele
Asymmetric construction of quaternary stereogenic centers via auxiliary-based SN2′ reactions: A case of 1,7-relative stereogenesis
Denmark, Scott E.,Marble, Lyndon K.
, p. 559 - 590 (2016/11/15)
The stereoselective construction of quaternary stereogenic centers is described that employs an allylic substitution through the intermediacy of a chiral carbamate leaving group. Five carbamates with two substituents at the allylic terminus combined with
Copper-free asymmetric allylic alkylation with a grignard reagent: Design of the ligand and mechanistic studies
Grassi, David,Dolka, Chrysanthi,Jackowski, Olivier,Alexakis, Alexandre
supporting information, p. 1466 - 1475 (2013/02/25)
The Cu-free asymmetric allylic alkylation, catalysed by NHC, with Grignard reagents is reported on allyl bromide derivatives with good results. The enantioselectivity was quite homogeneous (around 85 % ee) on large and various substrates, regardless of the nature of the Grignard reagent. The formation of stereogenic quaternary centres was highly regioselective for both aliphatic and aromatic derivatives with good enantiomeric excess (up to 92 % ee). The methodology developed was found to be complementary with the Cu-catalysed version. Several new NHCs were tested with improved efficiency. In addition, mechanistic studies, using NMR spectroscopy, led to the discovery of the catalytically active species. Copyright
Enantioselective synthesis of tertiary and quaternary stereogenic centers: Copper/phosphoramidite-catalyzed allylic alkylation with organolithium reagents
Fananas-Mastral, Martin,Perez, Manuel,Bos, Pieter H.,Rudolph, Alena,Harutyunyan, Syuzanna R.,Feringa, Ben L.
, p. 1922 - 1925 (2012/04/17)
An efficient and highly enantioselective copper-catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all-carbon quaternary stereogenic centers with these reactive organometallic reagents.
