5204-84-2Relevant articles and documents
Copper Hydride Catalyzed Enantioselective Synthesis of Axially Chiral 1,3-Disubstituted Allenes
Bayeh-Romero, Liela,Buchwald, Stephen L.
, p. 13788 - 13794 (2019/09/10)
The general enantioselective synthesis of axially chiral disubstituted allenes from prochiral starting materials remains a long-standing challenge in organic synthesis. Here, we report an efficient enantio- and chemoselective copper hydride catalyzed semireduction of conjugated enynes to furnish 1,3-disubstituted allenes using water as the proton source. This protocol is sufficiently mild to accommodate an assortment of functional groups including keto, ester, amino, halo, and hydroxyl groups. Additionally, applications of this method for the selective synthesis of monodeuterated allenes and chiral 2,5-dihydropyrroles are described.
An enantioselective synthesis of (R)-5,6-octadecadienoic acid
Yu, Qiong,Ma, Shengming
, p. 1596 - 1601 (2015/03/04)
A convenient, scalable, and highly enantioselective total synthesis of (R)-5,6-octadecadienoic acid was developed by using the recently established ATA (allenylation of terminal alkynes) reaction of TBS-protected (TBS = tert-butyldimethylsilyl) propargyl alcohol with n-dodecanal in the presence of (R)-α,α-diphenylprolinol as the chiral source. The axial chirality of the allene unit withstood the many common organic transformations that were needed to achieve the total synthesis with a high ee (enantiomeric excess) value.
