852998-62-0Relevant academic research and scientific papers
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
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.
Method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by one-pot method
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Paragraph 0047-0050; 0055; 0282-0292, (2020/12/15)
The invention relates to a method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by a one-pot method. The method comprises the following steps: making a racemic alpha-allyl alcohol compound, an amine compound, a chiral ruthenium complex and an alkaline reagent react in an organic solvent, and carrying out separation and purification after completion of the reaction, so that chiral gamma-aminoalcohols and chiral alpha-allylalcohol are prepared, wherein a chiral ruthenium complex is selected from one of them. According to the preparation method of the chiral compound, two chiral compounds with wide purposes, namely the chiral gamma-amino alcohol and the chiral alpha-allyl alcohol, are obtained at the same time through a one-pot reaction, the reaction is simple, the atom economy is high, few by-products are produced, and the requirements of green chemistry are met.
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
Asymmetric Synthesis of γ-Secondary Amino Alcohols via a Borrowing-Hydrogen Cascade
Chang, Xiaoyong,Chen, Fumin,He, Dongxu,Jin, Ming Yu,Pan, Yupeng,Xing, Xiangyou,You, Yipeng
supporting information, p. 7278 - 7283 (2020/10/02)
The borrowing-hydrogen (or hydrogen autotransfer) process, where the catalyst dehydrogenates a substrate and formally transfers the H atom to an unsaturated intermediate, is an atom-efficient and environmentally benign transformation. Described here is an example of an asymmetric borrowing-hydrogen cascade for the formal anti-Markovnikov hydroamination of allyl alcohols to synthesize optically enriched γ-secondary amino alcohols. By exploiting the Ru-(S)-iPrPyme catalyst with minimal stereogenicity, a cascade process including dehydrogenation, conjugate addition, and asymmetric reduction was developed. The mild conditions, functional group tolerance, and broad substrate scope (54 examples) demonstrate the synthetic practicality of the catalytic system.
A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols
Lin, Hui,Tang, Yanhong,Dong, Shuang,Lang, Ruibo,Chen, Hongge
, p. 2145 - 2151 (2020/04/17)
Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six st
Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs
Wang, Pei,Ma, Guo-Rong,Yu, Sheng-Li,Da, Chao-Shan
supporting information, p. 79 - 86 (2018/12/13)
Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.
Manganese-Catalyzed Ring-Opening Coupling Reactions of Cyclopropanols with Enones
Zhang, Yong-Hui,Zhang, Wen-Wei,Zhang, Ze-Yu,Zhao, Kai,Loh, Teck-Peng
supporting information, p. 5101 - 5105 (2019/07/03)
A manganese-catalyzed ring-opening coupling reaction of cyclopropanols with enones for the facile and efficient preparation of 1,6-diketones is described. A wide array of synthetically important 1,6-diketones bearing manifold functional groups are obtained with up to 93% yield. These reactions feature broad substrate scopes, environmentally benign conditions, inexpensive catalyst, and operational simplicity.
Efficient Pd-Catalyzed Regio- and Stereoselective Carboxylation of Allylic Alcohols with Formic Acid
Fu, Ming-Chen,Shang, Rui,Cheng, Wan-Min,Fu, Yao
supporting information, p. 8818 - 8822 (2017/07/11)
Formic acid is efficiently used as a C1 source to directly carboxylate allylic alcohols in the presence of a low loading of palladium catalyst and acetic anhydride as additive to afford β,γ-unsaturated carboxylic acids with excellent chemo-, regio-, and stereoselectivity. The reaction proceeds through a carbonylation process with in situ-generated carbon monoxide under mild conditions, avoiding the use of high-pressure gaseous CO. A bisphosphine ligand with a large bite angle (4,5-bis{diphenylphosphino}-9,9-dimethylxanthene, Xantphos) was found to be uniquely effective for this transformation. The regio- and stereoconvergence of this reaction is ascribed to the thermodynamically favored isomerization of the allylic electrophile in the presence of the palladium catalyst.
