58824-54-7Relevant academic research and scientific papers
Microwave-Assisted 1,3-Dioxa-[3,3]-Sigmatropic Rearrangement of Substituted Allylic Carbamates: Application to the Synthesis of Novel 1,3-Oxazine-2,4-dione Derivatives
Bou Zeid, Samar,Eid, Samar,Najjar, Fadia,Macé, Aurélie,Rivilla, Ivan,Cossío, Fernando P.,Dorcet, Vincent,Roisnel, Thierry,Carreaux, Fran?ois
supporting information, (2021/11/22)
In a first instance, the effect of the microwave irradiation on the 1,3-Dioxa-[3,3]-sigmatropic rearrangement of aryl allylic carbamates was investigated. Under these new conditions, the reaction acceleration was clearly highlighted compared to convention
Lanthanide-Catalyzed Tandem Addition of Amines to Cyanoalkenes: Synthesis of Cyclic Amidines
Hou, Jinsong,Yang, Gaosheng,Chai, Zhuo
supporting information, p. 453 - 463 (2022/01/04)
A tandem insertion of aliphatic nitriles and unactivated alkenes to the N-H bond of secondary aliphatic amines catalyzed by simple trialkyl rare-earth metal complexes was disclosed. This reaction provides a highly atom-economic and stereoselective way to a range of cyclic amidines under mild reaction conditions.
Iridium-Catalyzed Asymmetric Allylic Alkylation of Deconjugated Butyrolactams
Mitra, Sankash,Mukherjee, Santanu
supporting information, p. 3021 - 3026 (2021/05/04)
Compared with the ever-growing list of nonprochiral nucleophiles in Ir-catalyzed asymmetric allylic substitution reactions, prochiral nucleophiles are less studied. We present a new prochiral nucleophile, namely, deconjugated butyrolactam, for Ir-catalyze
Synthesis of C5-allylindoles through an iridium-catalyzed asymmetric allylic substitution/oxidation reaction sequence of N-alkyl indolines
Lu, Jiamin,Xu, Ruigang,Zeng, Haixia,Zhong, Guofu,Wang, Meifang,Ni, Zhigang,Zeng, Xiaofei
supporting information, p. 3426 - 3431 (2021/05/07)
Iridium/Br?nsted acid cooperative catalyzed asymmetric allylic substitution reactions at the C5 position of indolines have been reported for the first time. The highly efficient protocol allows rapid access to various C5-allylated products in good to high
Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol
Davis, Colton R.,Luvaga, Irungu K.,Ready, Joseph M.
supporting information, p. 4921 - 4927 (2021/05/04)
Alkenyl boronates add to Ir(π-allyl) intermediates with high enantioselectivity. A 1,2-metalate shift forms a second C-C bond and sets a 1,3-stereochemical relationship. The three-component coupling provides tertiary boronic esters that can undergo multiple additional functionalizations. An extension to trisubstituted olefins sets three contiguous stereocenters.
Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates
Wang, Lei,Wang, Lifan,Li, Mingxia,Chong, Qinglei,Meng, Fanke
supporting information, p. 12755 - 12765 (2021/08/30)
Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.
[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols
Chinnabattigalla, Sreenivasulu,Choudhury, Aditya,Gedu, Satyanarayana
supporting information, p. 8259 - 8263 (2021/10/12)
4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated fromDalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzedpara-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.
Direct and Selective Synthesis of Adipic and Other Dicarboxylic Acids by Palladium-Catalyzed Carbonylation of Allylic Alcohols
Beller, Matthias,Ge, Yao,Huang, Weiheng,Jackstell, Ralf,Liu, Jiawang,Neumann, Helfried,Yang, Ji
supporting information, p. 20394 - 20398 (2020/09/21)
A general and direct synthesis of dicarboxylic acids including industrially important adipic acid by palladium-catalyzed dicarbonylation of allylic alcohol is reported. Specifically, the combination of PdCl2 and a bisphosphine ligand (HeMaRaphos) promotes two different carbonylation reactions with high activity and excellent selectivity.
In Situ Ring-Closing Strategy for Direct Synthesis of N-Heterocyclic Carbene Nickel Complexes and Their Application in Coupling of Allylic Alcohols with Aryl Boronic Acids
Wang, Yu-Bin,Liu, Bin-Yuan,Bu, Qingqing,Dai, Bin,Liu, Ning
supporting information, p. 2930 - 2940 (2020/06/17)
A in situ ring-closing strategy was developed for the synthesis of N-heterocyclic carbene nickel complexes. The process was carried out in air, and did not require solvent purification. The resulting nickel complexes were investigated as catalysts for the coupling of allylic alcohols with aryl boronic acids. A wide range of allylic substrates and aryl acids proved to be applicable to this catalytic system. Control experiments suggest that the Ni(0) may be the true active species in the coupling reactions. (Figure presented.).
Synthesis of 2-(3-Arylallylidene)-3-oxindoles via Dirhodium(II)-Catalyzed Reaction of 3-Diazoindolin-2-imines with 1-Aryl-Substituted Allylic Alcohols and Computational Insights
Gao, Ke,Kou, Luyao,Fu, Rui,Bao, Xiaoguang
supporting information, p. 1292 - 1297 (2020/02/11)
A straightforward approach for the synthesis of 2-(3-arylallylidene)-3-oxindoles has been achieved by the dirhodium(II)-catalyzed reaction of 3-diazoindolin-2-imines with 1-aryl-substituted allylic alcohols. This protocol employs easily accessible feedsto
