752206-82-9Relevant academic research and scientific papers
Photo-Organocatalytic Enantioselective Radical Cascade Reactions of Unactivated Olefins
Bonilla, Pablo,Rey, Yannick P.,Holden, Catherine M.,Melchiorre, Paolo
, p. 12819 - 12823 (2018)
Radical cascade processes are invaluable for their ability to rapidly construct complex chiral molecules from simple substrates. However, implementing catalytic asymmetric variants is difficult. Reported herein is a visible-light-mediated organocatalytic strategy that exploits the excited-state reactivity of chiral iminium ions to trigger radical cascade reactions with high enantioselectivity. By combining two sequential radical-based bond-forming events, the method converts unactivated olefins and α,β-unsaturated aldehydes into chiral adducts in a single step. The implementation of an asymmetric three-component radical cascade further demonstrates the complexity-generating power of this photochemical strategy.
Niobium-Catalyzed Intramolecular Addition of O-H and N-H Bonds to Alkenes: A Tool for Hydrofunctionalization
Ferrand, Laura,Tang, Yue,Aubert, Corinne,Fensterbank, Louis,Mouriès-Mansuy, Virginie,Petit, Marc,Amatore, Muriel
, p. 2062 - 2065 (2017/04/28)
A convenient, versatile, and easy to handle intramolecular hydrofunctionalization of alkenes (C-O and C-N bonds formation) is reported using a novel niobium-based catalytic system. This atom economic and eco-friendly methodology provides an additional synthetic tool for the straightforward formation of valuable building blocks enabling molecular complexity. Various pyran, furan, pyrrolidine, piperidine, lactone, and lactam derivatives as well as spirocyclic compounds are produced in high yields and selectivities.
Direct catalytic anti-markovnikov hydroetherification of alkenols
Hamilton, David S.,Nicewicz, David A.
, p. 18577 - 18580 (2013/01/15)
A direct intramolecular anti-Markovnikov hydroetherification reaction of alkenols is described. By employing catalytic quantities of commercially available 9-mesityl-10-methylacridinium perchlorate and 2-phenylmalononitrile as a redox-cycling source of a
Intramolecular hydroalkoxylation in Bronsted acidic ionic liquids and its application to the synthesis of (±)-centrolobine
Jeong, Yunkyung,Kim, Do-Young,Choi, Yunsil,Ryu, Jae-Sang
supporting information; experimental part, p. 374 - 378 (2011/02/28)
The SO3H-tethered imidazolium and triazolium salts, nonvolatile and recyclable Bronsted acidic ionic liquids, efficiently mediate intramolecular hydroalkoxylations of alkenyl alcohols. They have been successfully employed in the synthesis of (±)-centrolobine.
Enantioselective cyclization of 4-alkenoic acids via an oxidative allylic C-H esterification
Takenaka, Kazuhiro,Akita, Mitsutoshi,Tanigaki, Yugo,Takizawa, Shinobu,Sasai, Hiroaki
, p. 3506 - 3509 (2011/09/12)
An enantioselective intramolecular oxidative cyclization of 4-alkenoic acids was developed. The reaction proceeded via a π-allyl Pd intermediate generated by an allylic C-H activation to give γ-lactone derivatives with moderate to good enantioselectivity. Spiro bis(isoxazoline) ligand, SPRIX, was indispensable for this asymmetric transformation.
Intramolecular additions of alcohols and carboxylic acids to inert olefins catalyzed by silver(I) triflate
Yang, Cai-Guang,Reich, Nicholas W.,Shi, Zhangjie,He, Chuan
, p. 4553 - 4556 (2007/10/03)
(Chemical Equation Presented) Intramolecular additions of hydroxyl or carboxyl groups to inert olefins catalyzed by simple silver(I) triflate are described. Good to excellent yields can be obtained for a range of substrates under relatively mild conditions. This reaction represents one of the simplest methods to construct cyclic ethers or lactones.
Platinum-catalyzed intramolecular hydroalkoxylation of γ- and δ-hydroxy olefins to form cyclic ethers
Qian, Hua,Han, Xiaoqing,Widenhoefer, Ross A.
, p. 9536 - 9537 (2007/10/03)
Reaction of 2,2-diphenyl-4-penten-1-ol with a catalytic mixture of [PtCl2(H2C=CH2)]2 (1 mol %) and P(4-C6H4CF3)3 (2 mol %) at 70 °C for 24 h led to the isolation of 2-
