144425-50-3Relevant academic research and scientific papers
Concise Allene Synthesis from Propargylic Alcohols by Hydrostannation and Deoxystannylation: A New Route to Chiral Allenes
Konoike, Toshiro,Araki, Yoshitaka
, p. 5093 - 5096 (1992)
Propargylic alcohols were converted to allenes in a two-step one-pot process comprised of hydrostannation of propargylic alcohols and subsequent deoxystannylation.Chiral (S)-2,3-decadiene of high enantiomeric excess (ee) can be prepared in a similar way.
Enantio- And Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis
Huo, Xiaohong,Ma, Shengming,Xiao, Junzhe,Zhang, Jiacheng,Zhang, Wanbin,Zhao, Ling
supporting information, p. 12622 - 12632 (2021/08/31)
In contrast to the widely explored methods for the asymmetric synthesis of molecules bearing a single stereocenter or adjacent stereocenters, the concurrent construction of 1,3-stereogenic centers in an enantio- and diastereoselective manner remains a challenge, especially in acyclic systems. Herein, we report an enantio- and diastereodivergent construction of 1,3-nonadjacent stereocenters bearing allenyl axial and central chirality through synergistic Pd/Cu-catalyzed dynamic kinetic asymmetric allenylation with racemic allenylic esters. The protocol is suitable for a wide range of substrates including the challenging allenylic esters with less sterically bulky substituents and provided chiral allenylic products bearing 1,3-nonadjacent stereocenters with high levels of enantio- and diastereoselectivities (up to >20:1 dr and >99% ee). Furthermore, several representative transformations involving axial-to-central chirality transfer were conducted, affording useful structural motifs containing nonadjacent stereocenters in a diastereodivergent manner.
Preparation of Chiral Allenes through Pd-Catalyzed Intermolecular Hydroamination of Conjugated Enynes: Enantioselective Synthesis Enabled by Catalyst Design
Adamson, Nathan J.,Jeddi, Haleh,Malcolmson, Steven J.
supporting information, p. 8574 - 8583 (2019/06/04)
In this study, we establish that conjugated enynes undergo selective 1,4-hydroamination under Pd catalysis to deliver chiral allenes with pendant allylic amines. Several primary and secondary aliphatic and aryl-substituted amines couple with a wide range of mono- and disubstituted enynes in a nonenantioselective reaction where DPEphos serves as the ligand for Pd. Benzophenone imine acts as an ammonia surrogate to afford primary amines in a two-step/one-pot process. Examination of chiral catalysts revealed a high degree of reversibility in the C-N bond formation that negatively impacted enantioselectivity. Consequently, an electron-poor ferrocenyl-PHOX ligand was developed to enable efficient and enantioselective enyne hydroamination.
Chromium(0)-Promoted [6π + 2π] cycloadditions of allenes with cycloheptatriene
Rigby, James H.,Laurent, Stephane B.,Kamal, Zeeshan,Heeg, Mary Jane
supporting information; experimental part, p. 5609 - 5612 (2009/06/18)
(Chemical Equation Presented) Photoinitiated [6π + 2π] cycloadditions of allenes with (η6-cycloheptatriene)tricarbonylchromium(0) (1) are described. An example of asymmetric induction obtained by reaction of 1 with a chiral 1,3-disubstituted al
