- Enantiopure cis- and trans-2-(2-Aminocyclohexyl)phenols: Effective Preparation, Solid-State Characterization, and Application in Asymmetric Organocatalysis
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Effective synthesis of cis- and trans-2-(2-methoxyphenyl)cyclohexylamine as well as their multigram-scale optical resolution by diastereomeric salt formation with dibenzoyl tartaric acid have been described. Assignment of absolute configurations to the enantiomers has been made by X-ray crystallography. Starting from the resolved precursor, diverse aminoalkylphenols (AAPs) having primary, secondary, and tertiary amine group as well as a quaternary ammonium phenol have been prepared as potential bifunctional organocatalysts based on the cyclohexane backbone. We furthermore report herein that AAPs carrying a primary amine and a phenolic hydroxyl group can catalyze the direct aldol reaction with high activity and setereoselectivity, and thus up to 97 % yield, 90:10 syn/anti diastereomeric ratio, and 80 % enantiomeric excess can be achieved.
- Tezeren, Mustafa A.,Ye?il, Tolga A.,Zorlu, Yunus,Tilki, Tahir,Ertürk, Erkan
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p. 7017 - 7032
(2018/12/13)
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- Arylalkene synthesis via decarboxylative cross-coupling of alkenyl halides
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A bimetallic catalyst system generated from readily available palladium(II) and copper(I) salts, 1,10-phenanthroline and tri-1-naphthylphosphine was found to efficiently mediate the decarboxylative cross-coupling of alkenyl bromides and chlorides with aromatic carboxylates. It allows the regiospecific synthesis of a broad range of aryl- and heteroarylalkenes in high yields.
- Tang, Jie,Goossen, Lukas J.
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p. 2664 - 2667
(2014/06/09)
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- N-heterocyclic carbene dichotomy in Pd-catalyzed acylation of aryl chlorides via C-H bond functionalization
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The first Pd-catalyzed intramolecular acylation of aryl chlorides via C-H bond functionalization is presented. The method allows for the synthesis of a variety of elusive benzocyclobutenones with a wide range of functional groups and substitution patterns. We demonstrate that a change in the ligand backbone dictates the selectivity pattern.
- Flores-Gaspar, Areli,Gutierrez-Bonet, Alvaro,Martin, Ruben
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supporting information
p. 5234 - 5237,4
(2012/12/12)
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- N-heterocyclic carbene dichotomy in Pd-catalyzed acylation of aryl chlorides via C-H bond functionalization
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The first Pd-catalyzed intramolecular acylation of aryl chlorides via C-H bond functionalization is presented. The method allows for the synthesis of a variety of elusive benzocyclobutenones with a wide range of functional groups and substitution patterns. We demonstrate that a change in the ligand backbone dictates the selectivity pattern.
- Flores-Gaspar, Areli,Gutierrez-Bonet, Alvaro,Martin, Ruben
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supporting information
p. 5234 - 5237
(2013/01/15)
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- FeCl3/Nal-catalyzed allylic C-H oxidation of arylalkenes with a catalytic amount of disulfide under air
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This paper describes a FeCl3/NaI-catalyzed formal allylic C-H oxidation of arylalkenes using a catalytic amount of disulfide with BnOH and 4-nitroaniline as nucleophiles and air as oxidant to form the corresponding allyl ethers and amines. A possible reaction mechanism has been proposed.
- Huang, Deshun,Wang, Haining,Xue, Fazhen,Shi, Yian
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body text
p. 7269 - 7274
(2011/10/09)
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- Well-defined air-stable palladium HASPO complexes for efficient Kumada-Corriu cross-couplings of (Hetero)aryl or alkenyl tosylates
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Palladium complexes of representative heteroatom-substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X-ray crystal structure analysis. Importantly, these well-defined complexes served as highly efficient catalysts for Kumada-Corriu cross-coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air-stable catalyst derived from inexpensive PinP(O)H displayed a remarkably high catalytic efficacy, which resulted in cross-couplings at low catalyst loadings under exceedingly mild reaction conditions with ample scope.
- Ackermann, Lutz,Kapdi, Anant R.,Fenner, Sabine,Kornhaab, Christoph,Schulzke, Carola
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supporting information; experimental part
p. 2965 - 2971
(2011/05/05)
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- Nickel-catalyzed cross-couplings of cyclohexenyl phosphate and arylboronic acids
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The Nickel-catalyzed cross-coupling reaction of cyclohexenylphosphate with a variety of arylboronic acids is described here for the first time. This methodology opens the door to other palladium or nickel-catalyzed coupling reactions involving vinyl phosphates.
- Nan, Yang,Yang, Zhen
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p. 3321 - 3324
(2007/10/03)
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