35281-62-0Relevant academic research and scientific papers
Copper-Catalyzed Direct and Stereoselective Synthesis of Conjugated Enynes from α-Allenols
Sai, Masahiro,Matsubara, Seijiro
supporting information, p. 39 - 43 (2018/11/23)
A novel strategy for the stereoselective synthesis of conjugated enynes directly from α-allenols has been developed. The reaction proceeds with perfect E-selectivity and exhibits high functional group compatibility. This catalytic system can also be applied to the stereoselective synthesis of conjugated dienynes and enediynes. (Figure presented.).
An efficient CuCN-catalyzed synthesis of optically active 2,3-allenols from optically active 1-substituted 4-chloro-2-butyn-1-ols
Li, Jing,Kong, Wangqing,Fu, Chunling,Ma, Shengming
supporting information; experimental part, p. 5104 - 5106 (2009/10/17)
(Chemical Equation Presented) The sequential treatment of optically active terminal propargylic alcohols with n-BuLi/(HCHO)n and regioselective chlorination afforded the corresponding optically active 4-chloro-2-butyn-1-ols. With R1
Studies on Cu(I)-catalyzed synthesis of simple 3-substituted 1,2-allenes and optically active 2-substituted secondary 2,3-allenols
Li, Jing,Zhou, Chao,Fu, Chunling,Ma, Shengming
experimental part, p. 3695 - 3703 (2009/09/05)
The sequential treatment of terminal alkynes or propargylic alcohols with n-BuLi and MOMCl afforded the corresponding propargylic methyl ethers, which would react with primary alkyl Grignard reagents under the catalysis of CuBr to afford 3-substituted 1,2-allenes or 2-substituted secondary 2,3-allenols, respectively. The reaction may be applied to the synthesis of optically active 2-substituted secondary 2,3-allenols with up to >99% ee without any protection to the free hydroxyl group in the starting 4-hydroxy-2-alkynyl methyl ethers.
Studies on electrophilic interaction of 2,3-allenols with electrophilic halogen reagents: Selective synthesis of 2,5-dihydrofurans, 3-halo-3-alkenals, or 2-halo-2-alkenyl ketones
Li, Jing,Fu, Chunling,Chen, Guofei,Chai, Guobi,Ma, Shengming
supporting information; experimental part, p. 1376 - 1382 (2009/07/09)
The reaction of primary 2,3-allenols with iodine (I2) afforded 2,5-dihydrofurans while that of readily available 1-aryl or 1-methyl substituted 2,3-allenols with bromine (Br2), N-bromosuccinimide (NBS), I 2 or N-iodosuccin
PdI2-catalyzed coupling-cyclization reactions involving two different 2,3-allenols: An efficient synthesis of 4-(1′,3′-dien- 2′-yl)-2,5-dihydrofuran derivatives
Deng, Youqian,Li, Jing,Ma, Shengming
supporting information; experimental part, p. 4263 - 4266 (2009/05/07)
Transition-metal-catalyzed dimeric coupling-cyclization reactions of two different 2,3-allenols afforded 4-(1′,3′-dien-2′-yl)-2,5- dihydrofuran derivatives 3. 2-Substituted 2,3-allenols 1 cyclized to form the 2,5-dihydrofuran ring, whereas the 2-unsubstit
Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans and 5,6-dihydro-2H-pyrans via the Pd-catalyzed cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides
Ma, Shengming,Gao, Wenzhong
, p. 6104 - 6112 (2007/10/03)
In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)2, Pd(OAc)2, and [(π-C3H5)PdCl]2, can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.
General method for preparation of allenic zinc reagents by three-carbon homologation of triorganozincates: Convergent three-component coupling of propargylic substrates, triorganozincates, and electrophilic reagents
Harada, Toshiro,Katsuhira, Takeshi,Osada, Atsushi,Iwazaki, Katsuhiro,Maejima, Keiji,Oku, Akira
, p. 11377 - 11390 (2007/10/03)
Allenic zinc reagents (R1R2C=C=C(R3)ZnL) are efficiently prepared by the reaction of propargylic substrates (R1R2C(X)C≡CH, X = MeSO2O,Cl, R2NCO2) with a variety of tri
Preparation of Polyfunctional Allenic Alcohols by the Regioselective Addition of Functionalized Propargylic Chromium(III) Organometallics to Carbonyl Compounds
Belyk, Kevin,Rozema, Michael J.,Knochel, Paul
, p. 4070 - 4074 (2007/10/02)
The reaction of propargylic halides 1 (X = Cl, Br) with an aldehyde or ketone (0.67 equiv) in the presence of CrCl2 (2.0 equiv) and LiI (2 equiv, necessary if X = Cl) affords allenic alcohols 3 with excellent regioselectivities (3-6percent of the regioiso
