91154-05-1Relevant academic research and scientific papers
Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil
Oliveira, Caio C.,Pfaltz, Andreas,Correia, Carlos Roque Duarte
, p. 14036 - 14039 (2015)
We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine- and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.
A NEW SYNTHESIS OF trans-2-SUBSTITUTED-2-BUTENE-1,4-DIOLS FROM 2-BUTYNE-1,4-DIOL VIA NUCLEOPHILIC ADDITION OF GRIGNARD REAGENTS
Ishino, Yoshio,Wakamoto, Kohji,Hirashima, Tsuneaki
, p. 765 - 768 (2007/10/02)
trans-2-Substituted-2-butene-1,4-diols were readily obtained by reactions of 2-butyne-1,4-diol with Grignard reagents in good yields.
