27694-87-7Relevant academic research and scientific papers
Room Temperature Allenation of Terminal Alkynes with Aldehydes
Cui, Yifan,Li, Can,Ma, Shengming,Xiao, Junzhe,Xu, Haibo,Zhai, Yizhan,Zhang, Xue
, p. 25708 - 25713 (2021/11/09)
A gold-catalyzed room temperature allenation of terminal alkynes (ATA) with aldehydes affording 1,3-disubstituted allenes with diverse functional groups has been developed by identifying a gold(I) catalyst and an amine. The practicality of this reaction has been demonstrated by a ten gram-scale synthesis and the synthetic potentials have been demonstrated via various transformations and formal total synthesis of (?)-centrolobine. Mechanistic studies revealed that the gold catalyst, the aldehyde effect, the fluoroalkyl hydroxyl solvent (TFE or HFIP) and the structure of amine are vital in this room temperature ATA reaction.
Gold-Catalyzed One-Pot Synthesis of 1,3-Disubstituted Allenes from Benzaldehydes and Terminal Alkynes
Lustosa, Danilo M.,Clemens, Simon,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information, p. 5050 - 5056 (2019/11/05)
A new and facile one-pot synthesis of 1,3-disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up t
Bimetallic enantioselective approach to axially chiral allenes
Lue, Ruizhi,Ye, Juntao,Cao, Tao,Chen, Bo,Fan, Wu,Lin, Weilong,Liu, Jinxian,Luo, Hongwen,Miao, Bukeyan,Ni, Shengjun,Tang, Xinjun,Wang, Nan,Wang, Yuli,Xie, Xi,Yu, Qiong,Yuan, Weiming,Zhang, Wanli,Zhu, Can,Ma, Shengming
supporting information, p. 2254 - 2257 (2013/06/05)
An efficient bimetallic Zn(II)/Cu(I)-mediated asymmetric synthesis of simple axially chiral allenes from terminal alkynes and aldehydes was realized by taking advantage of the chiral amine (S)-α,α-diphenylprolinol 3. This one-pot procedure is compatible w
CuI-catalyzed cross-coupling of N-tosylhydrazones with terminal alkynes: Synthesis of 1,3-disubstituted allenes
Hossain, Mohammad Lokman,Ye, Fei,Zhang, Yan,Wang, Jianbo
, p. 1236 - 1241 (2013/04/10)
A CuI-catalyzed synthesis of 1,3-disubstituted allenes from 1-alkynes by the reaction with various N-tosylhydrazones has been developed. This method, which uses readily available starting materials and is operationally simple, offers 1,3-disubstituted all
Asymmetric dihydroxylation of disubstituted allenes
Fleming, Steven A.,Liu, Renmao,Redd, J. Ty
, p. 8095 - 8098 (2007/10/03)
Asymmetric dihydroxylation of 1,1-disubstituted and 1,3-disubstituted allenes can be used to synthesize chiral α-hydroxy ketones. We have also obtained α,α′-dihydroxy ketones with high enantioselectivity from 1,3-disubstituted allenes. Low conversion of the dihydroxylation of chiral allenes can be used as a kinetic resolution of sterically hindered allenes.
Allenes from ynals
Tius, Marcus A.,Pal, Subrata K.
, p. 2605 - 2608 (2007/10/03)
Hydrosilylation of ynals with triethylsilane is catalyzed by RhCl(PPh3)3 and leads to α-triethylsilyl enals. Addition of aryl Grignard reagents takes place to give secondary allylic alcohols which are easily converted to 1,3-disubstituted allenes.
Highly Stereoselective Synthesis of Chiral Alkylallenes by Organocopper(I)-Induced Anti 1,3-Substitution of Chiral Propynyl Esters
Elsevier, Cornelis J.,Vermeer, Peter
, p. 3726 - 3730 (2007/10/02)
The synthesis of chiral 1,3-dialkylallenes R1CH=C=CHR2 of high enantiomeric purity, by applying homogeneous reaction between organocopper(I) reagents of type 2CuX>MgX-LiX> and chiral propynyl methanesulfonates or sulfinates at low temperatures in THF, is reported.The reactions are generally fast; typically complete conversion is obtained within a few minutes at -60 deg C.Overall, high anti stereoselectivity is observed.A plausible mechanism is put forward, and comparison is made with the stereochemistry of reactions of comparable substrates with d10 complexes, e.g. of Pd(0).
