29805-12-7Relevant academic research and scientific papers
Allenylidene Induced 1,2-Metalate Rearrangement of Indole-Boronates: Diastereoselective Access to Highly Substituted Indolines
Simlandy, Amit Kumar,Brown, M. Kevin
supporting information, p. 12366 - 12370 (2021/05/03)
A process to achieve 1,2-metalate rearrangements of indole boronate as a way to access substituted indolines in high diastereoselectivities is presented. The reaction involves the generation of a Cu–allenylidene, which is sufficiently electrophilic to induce the 1,2-metalate rearrangement. The scope of the reaction is evaluated as well as further transformations of the product.
Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones
He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo
, p. 457 - 466 (2021/01/29)
An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is
Synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by a palladium-catalyzed three-component reaction
Horino, Yoshikazu,Sakamoto, Juri,Murakami, Miki,Sugata, Miki
supporting information, p. 1323 - 1327 (2020/08/21)
A synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by using a palladium-catalyzed three-component reaction has been developed. This method shows good functional-group compatibility and generality, with high diastereoselectivity. Additionally, in many cases, the present method controls the alkene stereochemistry of the newly formed C-C bond and overcomes the inherent preference for (E)-alkene formation, giving (Z, E)- and (Z, Z)-products.
Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines
Mao, Biming,Zhang, Junya,Xu, Yi,Yan, Zhengyang,Wang, Wei,Wu, Yongjun,Sun, Changqing,Zheng, Bing,Guo, Hongchao
supporting information, p. 12841 - 12844 (2019/11/05)
In this paper, a palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine under cocatalysis of Ag(i)/Pd(0) catalysts in a similar reaction pathway.
Enantioselective Propargylation of Polyols and Desymmetrization of meso 1,2-Diols by Copper/Borinic Acid Dual Catalysis
Li, Ren-Zhe,Tang, Hua,Yang, Ke R.,Wan, Li-Qiang,Zhang, Xia,Liu, Jie,Fu, Zhengyan,Niu, Dawen
supporting information, p. 7213 - 7217 (2017/06/13)
A copper/borinic acid dual catalytic reaction enabled the enantioselective propargylation of aliphatic polyols. Readily available reagents and catalysts were used in this transformation, which displayed good to excellent chemo- and stereoselectivity for a broad array of substrates. The method was also applicable to the desymmetrization of meso 1,2-diols to furnish products with three stereogenic centers and a terminal alkyne group in one operation.
Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach
Li, Wenhua,Lin, Zuming,Chen, Long,Tian, Xuechao,Wang, Yan,Huang, Sha-Hua,Hong, Ran
supporting information, p. 603 - 606 (2016/01/20)
A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.
Br?nsted acid-catalyzed meyer-schuster rearrangement for the synthesis of α, β -unsaturated carbonyl compounds
Park, Jungmin,Yun, Jihee,Kim, Jaehyun,Jang, Dong-Jin,Park, Cheol Ho,Lee, Kooyeon
supporting information, p. 1924 - 1929 (2014/07/07)
An efficient and simple protocol for the Meyer-Schuster rearrangement of propargyl alcohols into α,β-unsaturated carbonyl compounds has been developed using catalytic amounts of p-toluenesulfonic acid in 1,2-dichloroethane.
Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols
Wang, Yan,Zheng, Kuan,Hong, Ran
supporting information; scheme or table, p. 4096 - 4099 (2012/04/10)
A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.
Palladacycle-catalyzed reaction of bicyclic alkenes with terminal ynones: Regiospecific synthesis of polysubstituted furans
Ge, Guang-Cun,Mo, Dong-Liang,Ding, Chang-Hua,Dai, Li-Xin,Hou, Xue-Long
, p. 5756 - 5759 (2013/01/15)
A new synthetic strategy to access polysubstituted furans regiospecifically has been developed using simple bicyclic alkenes and terminal ynones as starting materials with palladacycles as unique active catalysts. A rational mechanism has also been proposed. This reaction features mild reaction conditions, easily available starting materials and palladacycle catalysts, a wide substrate scope, and high regiospecificity.
Base-catalyzed cascade 1,3-H shift/cyclization reaction to construct polyaromatic furans
Wang, Ya-Hui,Liu, Heng,Zhu, Li-Li,Li, Xiao-Xiao,Chen, Zili
, p. 707 - 712 (2011/05/06)
A convenient new method was developed to prepare unfused polyaromatic furan derivatives from diynyl-1,6-diols through a novel base-catalyzed cascade 1,3-H shift/cyclization process. Deuterium experiments were performed to determine that the 1,3-H shift was the rate-determining step. Copyright
