149946-79-2Relevant academic research and scientific papers
Catalytic Asymmetric Intramolecular Bromolactonization of α,β-Unsaturated Ketones
Gan, Min,He, Hailong,Jiang, Xiaojian,Liu, Shenghui,Yi, Peng
, p. 1474 - 1478 (2019)
Enantioselective bromolactonization by using an amino-urea catalyst to generate the important bromo-containing 3,4-dihydroisocoumarins is described. Excellent yields and good enantioselectivities could be achieved for various 3,4-dihydroisocoumarin compou
Rh-Catalyzed Regioselective Dialkylation of Cage B-H bonds in o-Carboranes: Oxidative Heck Reactions via an Enol Isomerization
Wang, Qian,Tian, Song,Zhang, Chuyi,Li, Jiangwei,Wang, Zhixuan,Du, Yongmei,Zhou, Ling,Lu, Jian
, p. 8018 - 8021 (2019)
In the presence of a carboxylic acid directing group, Rh-catalyzed regioselective directed dialkylation of B(4,5)-H bonds in o-carboranes and oxidative coupling with allylic alcohols is reported. This strategy constructs a series of 4,5-dialkylated o-carboranes in good yields with excellent regioselectivity. A possible catalytic cycle is proposed that involves a tandem sequence of Rh-catalyzed cage B-H activation, alkene insertion, selective β-H elimination, enol isomerization, and decarboxylation.
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
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.
Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones
Zhang, Ninghui,Zhang, Chunli,Hu, Xiaoping,Xie, Xin,Liu, Yuanhong
supporting information, p. 6004 - 6009 (2021/07/31)
An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.
Pd-Catalyzed Asymmetric Acyl-Carbamoylation of an Alkene to Construct an α-Quaternary Chiral Cycloketone
Liu, Min,Wang, Xing,Guo, Ziqiong,Li, Hanyuan,Huang, Wei,Xu, Hui,Dai, Hui-Xiong
supporting information, p. 6299 - 6304 (2021/08/30)
Herein, we report the palladium-catalyzed asymmetric acyl-carbamoylation of an alkene by employing thioesters as the acyl electrophiles and t-BuNC as the carbamoyl reagent, affording an α-quaternary chiral cycloketone in synthetically useful yields with excellent enantioselectivity. The reaction proceeded via asymmetric 1,2-migratory insertions of acyl-Pd into alkenes and subsequent migratory insertion of isocyanides into C(sp3)-PdII. The product could be diversified to some valuable skeletons with retention of enantiopurity, demonstrating the synthetic utility of this protocol.
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.
Nickel-Catalyzed Reductive Csp2-Csp3Cross Coupling Using Phosphonium Salts
Liang, Hongze,Lu, Xinyao,Luo, Yunjie,Man, Xi,Mou, Zehuai,Wang, Huifei,Wang, Yuting,Yang, Mengwan
supporting information, p. 8183 - 8188 (2021/11/13)
A nickel-catalyzed reductive cross coupling with phosphonium salts and allylic C(sp3)-O bond electrophiles, which granted direct construction of the C(sp2)-C(sp3) bond, is successfully developed. The protocol features broad substrate scope, high-functional-group tolerance, and heterocycle compatibility. Notably, the much more challenging reductive cross coupling with heterocyclic thiazolylphosphonium salts has also been accomplished for the first time.
Highly efficient kinetic resolution of aryl-alkenyl alcohols by ru-catalyzed hydrogen transfer
Jin, Ming Yu,Tao, Guanyu,Xing, Xiangyou,You, Yipeng
supporting information, (2021/12/24)
No matter through asymmetric reduction of ketones or kinetic resolution of secondary alcohols, enantioselective synthesis of the corresponding secondary alcohols is challenging when the two groups attached to the prochiral or chiral centers are spatially
