146983-99-5Relevant academic research and scientific papers
Synthesis of Allenes via Palladium-Catalyzed Hydrogen-Transfer Reactions: Propargylic Amines as an Allenyl Anion Equivalent
Nakamura, Hiroyuki,Kamakura, Takaya,Ishikura, Makoto,Biellmann, Jean-Francois
, p. 5958 - 5959 (2004)
Synthesis of allenes has been achieved by using palladium-catalyzed hydrogen-transfer reactions. Various propargylic amines, which were readily prepapred from iodobenzenes and propargylic amines by Sonogashira coupling reaction, underwent the hydrogen-tra
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
, 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.
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
, 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
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
Zinc-catalyzed allenylations of aldehydes and ketones
Fandrick, Daniel R.,Saha, Jaideep,Fandrick, Keith R.,Sanyal, Sanjit,Ogikubo, Junichi,Lee, Heewon,Roschangar, Frank,Song, Jinhua J.,Senanayake, Chris H.
supporting information; experimental part, p. 5616 - 5619 (2011/12/03)
The general zinc-catalyzed allenylation of aldehydes and ketones with an allenyl boronate is presented. Preliminary mechanistic studies support a kinetically controlled process wherein, after a site-selective B/Zn exchange to generate a propargyl zinc int
A simple approach to separate a mixture of homopropargylic and allenic alcohols
Fu, Fan,Hoang, Kim Le Mai,Loh, Teck-Peng
supporting information; experimental part, p. 3437 - 3439 (2009/05/07)
(Chemical Equation Presented) A simple and practical approach to separate homopropargylic alcohol from allenic alcohol has been developed. It involves the formation of an insoluble silver acetylide species between silver nitrate and homopropargylic alcohol in aqueous acetone which can be separated from the allenic alcohol through a simple filtration. The homopropargylic alcohol can subsequently be recovered by hydrolysis with 1 N HCl. This protocol has been applied to the separation of a mixture of chiral homopropargylic and allenic alcohols in excellent yields with retention of absolute stereochemistry.
Synthesis of mono- and 1,3-disubstituted allenes from propargylic amines via palladium-catalysed hydride-transfer reaction
Nakamura, Hiroyuki,Ishikura, Makoto,Sugiishi, Tsuyuka,Kamakura, Takaya,Biellmann, Jean-Francois
experimental part, p. 1471 - 1477 (2008/10/09)
Mono- and 1,3-disubstituted allenes were synthesized from the corresponding propargylamines via palladium-catalysed hydride-transfer reaction. In the current transformation, propargylic amines can be handled as allenyl anion equivalents and introduced int
