854493-96-2Relevant academic research and scientific papers
A stereoselective approach to 1,3-amino alcohols protected as cyclic carbamates: Kinetic vs. thermodynamic control
Broustal, Garance,Ariza, Xavier,Campagne, Jean-Marc,Garcia, Jordi,Georges, Yohan,Marinetti, Angela,Robiette, Raphael
, p. 4293 - 4297 (2007)
Direct enantiocontrolled access to 1,3-amino alcohols protected as cyclic carbamates is described. The approach is based on the addition of a silyl dienolate to aldehydes in the presence of 10 % of Carreira's catalyst (vinylogous Mukaiyama-aldol addition)
Catalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones: Formal asymmetric synthesis of taurospongin A
Moreau, Xavier,Bazan-Tejeda, Belen,Campagne, Jean-Marc
, p. 7288 - 7289 (2005)
Catalytic asymmetric vinylogous Mukaiyama reactions on ketones, leading to the formation of α,β-unsaturated lactones with tertiary alcohols, have been described (11 examples, up to 93% ee). This methodology has been applied in a formal enantioselective sy
Concise enantioselective synthesis of δ,δ-disubstituted δ-valerolactones
Saito, Akira,Kumagai, Naoya,Shibasaki, Masakatsu
, p. 3167 - 3171 (2014/05/20)
Efficient access to enantioenriched δ,δ-disubstituted δ-valerolactones is described. A soft Lewis acid/hard Br?nsted base cooperative catalyst allowed for direct catalytic asymmetric γ-addition of allyl cyanide to ketones, producing tertiary homoallylic alcohols with a Z-configured α,β-unsaturated nitrile. Electrophilic activation of the nitrile functionality triggered 6-exo-dig cyclization, and subsequent N-acylation gave rise to the δ-valerolactone skeleton via CN bond cleavage.
