91671-36-2Relevant academic research and scientific papers
Cobalt-Catalyzed C8-Dienylation of Quinoline-N-Oxides
Khan, Salman,Nair, Akshay M.,Shukla, Rahul K.,Volla, Chandra M. R.
supporting information, p. 17042 - 17048 (2020/08/05)
An efficient Cp*CoIII-catalyzed C8-dienylation of quinoline-N-oxides was achieved by employing allenes bearing leaving groups at the α-position as the dienylating agents. The reaction proceeds by CoIII-catalyzed C?H activation of qui
Regioselectivity Switch in Palladium-Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross-Coupling
Li, Long,Luo, Pengfei,Deng, Yuhua,Shao, Zhihui
supporting information, p. 4710 - 4713 (2019/03/08)
The first Pd-catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross-coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds led to the discovery of new antitumor targets. A possible mechanism is proposed, suggesting two interesting catalytic cycles for the cycloaddition with palladium-butadienyls. This study also demonstrated the potential and utility of allenic esters as 1,4-biselectrophiles and C4 synthons for participating in cycloaddition reactions.
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.
Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations
Petrone, David A.,Isomura, Mayuko,Franzoni, Ivan,R?ssler, Simon L.,Carreira, Erick M.
supporting information, p. 4697 - 4704 (2018/04/11)
An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p
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.
Enzyme- and Ruthenium-Catalyzed Enantioselective Transformation of α-Allenic Alcohols into 2,3-Dihydrofurans
Yang, Bin,Zhu, Can,Qiu, Youai,B?ckvall, Jan-E.
supporting information, p. 5568 - 5572 (2016/05/09)
An efficient one-pot method for the enzyme- and ruthenium-catalyzed enantioselective transformation of α-allenic alcohols into 2,3-dihydrofurans has been developed. The method involves an enzymatic kinetic resolution and a subsequent ruthenium-catalyzed c
Dehydrative thiolation of allenols: Indium vs gold catalysis
Webster,Young,Barker,Rosair,Lee
, p. 1703 - 1718 (2015/02/19)
Intermolecular additions of thiols to allenols via formal SN2 selectivity to produce functionalized dienes are described. Although this dehydrative reaction was initially developed using gold(I) catalysis, indium(III) proves to be a far superio
Bu4N+ alkoxide-initiated/autocatalytic addition reactions with organotrimethylsilanes
Das, Manas,O'Shea, Donal F.
, p. 5595 - 5607 (2014/07/08)
The use of Me3SiO-/Bu4N+ as a general activator of organotrimethylsilanes for addition reactions has been established. The broad scope of the method offers trimethylsilanes (including acetate, allyl, propargyl, benzyl, dithiane, heteroaryl, and aryl derivatives) as bench-stable organometallics that can be readily utilized as carbanion equivalents for synthesis. Reactions are achieved at rt without the requirement of specialized precautions that are commonplace for other organometallics.
A general approach to terminal allenols
Kuang, Jinqiang,Xie, Xi,Ma, Shengming
supporting information, p. 592 - 595 (2013/04/10)
We have demonstrated a very general method for the preparation of essentially any terminal 2,3-allenol from the corresponding alkynols, which may be easily available from propargylic alcohols by alkylation, or from terminal alkynes by deprotonation and 1,
CuI-catalyzed synthesis of functionalized terminal allenes from 1-alkynes
Luo, Hongwen,Ma, Shengming
, p. 3041 - 3048 (2013/06/27)
Relative to our original protocol that uses CuI (0.5 equiv.), paraformaldehyde (2.5 equiv.), and dicyclohexylamine (1.8 equiv.), a facile and efficient protocol for the gram-scale synthesis of functionalized terminal allenes by using CuI (7.5-10 mol-%), p
