74268-51-2Relevant articles and documents
Synthesis of chiral diferrocenyl diselenides and their application to asymmetric reactions
Nishibayashi,Nishibayashi, Yoshiaki,Singh,Singh, Jai Deo,Uemura,Uemura, Sakae,Fukuzawa,Fukuzawa, Shin-Ichi
, p. 3115 - 3118 (1994)
Two optically active diferrocenyl diselenides, each of which possesses two chiral centers, were newly prepared from commercial 1-(dimethylamino)ethylferrocenes and applied to induce highly enantioselective selenoxide elimination producing axially chiral allenecarboxylic esters.
PPh3-catalyzed β-selective addition of α-fluoro β-dicarbonyl compounds to allenoates
Liu, Yong-Liang,Wang, Xiao-Ping,Wei, Jie,Li, Ya
supporting information, (2021/12/02)
A highly selective phosphine-catalyzed β-addition of α-fluoro β-dicarbonyl compounds to allenoates has been developed. Both α-fluoro β-diketones and α-fluoro β-keto esters prove to be competent fluorocarbon nucleophiles, giving a series of the β-addition products bearing a fluorinated quaternary carbon center in good to excellent yields and with excellent regioselectivities. A plausible reaction pathway is presented.
Phosphine-Catalyzed Asymmetric Tandem Isomerization/Annulation of Allyl Amines with Allenoates: Enantioselective Annulation of a Saturated C-N Bond
Zhou, Leijie,Zhang, Xue,Wang, Qijun,Liu, Min,Wang, Wei,Wu, Yongjun,Chen, Liezhong,Guo, Hongchao
supporting information, p. 9173 - 9178 (2021/11/30)
Under catalysis by chiral phosphine, an asymmetric isomerization/annulation cascade reaction of allylamines with allenoates was realized. A wide range of γ-substituted allenoates were tolerated to afford chiral pyrroline derivatives in high yields with excellent enantioselectivities. In the reaction, isomerization of readily available N-allylamines to reactive aliphatic imines through a 1,4-proton shift is a key step, which circumvents the isolation of highly unstable alkyl N-sulfonylimines.
NHC-Catalyzed Aldol-Like Reactions of Allenoates with Isatins: Regiospecific Syntheses of γ-Functionalized Allenoates
Li, Sha,Tang, Ziwei,Wang, Yang,Wang, Dan,Wang, Zhanlin,Yu, Chenxia,Li, Tuanjie,Wei, Donghui,Yao, Changsheng
supporting information, p. 1306 - 1310 (2019/02/26)
An N-heterocyclic carbene (NHC) catalyzed γ-specific aldol-like reaction between allenoates and isatins has been achieved under mild conditions, giving trisubstituted allene derivatives bearing isatin moiety in moderate to good yields with high diastereoselectivity and excellent atom efficiency. The DFT computations indicated that the formation of the γ-adduct was more energetically favorable than that of the α-adduct. The result reported herein opens a new route for NHC-promoted allenoate-involved reaction.
Metal-Free Transfer Hydroiodination of C-C Multiple Bonds
Chen, Weiqiang,Walker, Johannes C. L.,Oestreich, Martin
supporting information, p. 1135 - 1140 (2019/01/11)
The design and a gram-scale synthesis of a bench-stable cyclohexa-1,4-diene-based surrogate of gaseous hydrogen iodide are described. By initiation with a moderately strong Br?nsted acid, hydrogen iodide is transferred from the surrogate onto C-C multiple bonds such as alkynes and allenes without the involvement of free hydrogen iodide. The surrogate fragments into toluene and ethylene, easy-to-remove volatile waste. This hydroiodination reaction avoids precarious handling of hydrogen iodide or hydroiodic acid. By this, a broad range of previously unknown or difficult-to-prepare vinyl iodides can be accessed in stereocontrolled fashion.
Phosphine-catalyzed regiodivergent annulations of γ-substituted allenoates with conjugated dienes
Gan, Zhenjie,Gong, Yanchuan,Chu, Yunpeng,Li, Er-Qing,Huang, You,Duan, Zheng
, p. 10120 - 10123 (2019/08/30)
A phosphine catalyzed regiodivergent annulation of γ-substituted allenoates with conjugated dienes is reported, and highly functionalized cyclohexenes or cyclopentenes were obtained in high yields and regioselectivities. This transformation takes advantag
Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols
Panchal, Heena,Clarke, Christopher,Bell, Charles,Karad, Somnath Narayan,Lewis, William,Lam, Hon Wai
supporting information, p. 12389 - 12392 (2018/11/20)
Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.
Efficient and regioselective one-pot synthesis of S-vinyl dithiocarbamates from electron-deficient allenes, amines and CS2
Li, Ridong,Leng, Penglin,Liu, Bin,Wang, Xin,Ge, Zemei,Li, Runtao
supporting information, p. 5707 - 5712 (2016/08/23)
A novel and efficient one-pot procedure for the synthesis of S-vinyl dithiocarbamates from electron-deficient allenes, amines and CS2was presented. The reactions proceed at room temperature for 10–30?min without any catalyst to afford the products in high yields, excellent regioselectivity and stereoselectivity.
Highly enantioselective, intermolecular hydroamination of allenyl esters catalyzed by bifunctional phosphinothioureas
Fang, Yuan-Qing,Tadross, Pamela M.,Jacobsen, Eric N.
supporting information, p. 17966 - 17968 (2015/03/03)
Bifunctional phosphinothiourea catalysts have been developed successfully for the highly regio- and enantioselective γ-hydroamination of allenyl and propargyl esters with N-methoxy carbamate nucleophiles to yield α,β-unsaturated γ-amino acid ester products. In the case of propargyl ester substrates, the reaction proceeds through reversible phosphinothiourea-catalyzed isomerization to the corresponding allenyl ester. The high enantioselectivity of the process is attributed to a cooperative conjugate addition of a thiourea-bound carbamate anion to a vinyl phosphonium ion resulting from covalent activation of the allenyl ester substrate.
Copper-catalyzed, C-C coupling-based one-pot tandem reactions for the synthesis of benzofurans using o-iodophenols, acyl chlorides, and phosphorus ylides
Liu, Yunyun,Wang, Hang,Wan, Jie-Ping
, p. 10599 - 10604 (2015/02/19)
One-pot reactions involving acyl chlorides, phosphorus ylides, and o-iodophenols with copper catalysis have been established for the rapid synthesis of functionalized benzofurans. With all of these easily available and stable reactants, the construction o
