937237-78-0Relevant academic research and scientific papers
Coordination-Induced Stereocontrol over Carbocations: Asymmetric Reductive Deoxygenation of Racemic Tertiary Alcohols
Isomura, Mayuko,Petrone, David A.,Carreira, Erick M.
supporting information, p. 4738 - 4748 (2019/03/19)
The inherent difficulty in eliciting facial control over carbocations has limited their utility as intermediates in asymmetric catalysis. We have now shown that a docking strategy involving the reversible coordination of a substrate to a chiral transition-metal catalyst can be used to enable highly stereoselective nucleophilic attack on intermediate tertiary carbocations. This approach has been implemented to achieve the first example of enantioselective reductive deoxygenation of tertiary alcohols. This reduction occurs with high enantio- (up to 96% ee) and regioselectivity (up to >50:1 rr) by applying a novel Hantzsch ester analogue as a convenient hydride source. In-depth mechanistic studies support the involvement of a tertiary carbocation that is coordinated to the iridium metal center via the key allene moiety.
Ruthenium-catalyzed reactions of 1-cyclopropyl-2-propyn-1-ols with anilines and water via allenylidene intermediates: Selective preparation of tri- and tetrasubstituted conjugated enynes
Yamauchi, Yoshihiro,Onodera, Gen,Sakata, Ken,Yuki, Masahiro,Miyake, Yoshihiro,Uemura, Sakae,Nishibayashi, Yoshiaki
, p. 5175 - 5179 (2008/02/01)
Ruthenium-catalyzed efficient preparation of the conjugated enynes can be carried out in the reactions of 1-cyclopropyl-2-propyn-1-ols with nitrogen- and oxygen-centered nucleophiles such as anilines and water in the presence of a catalytic amount of sulf
