Masaaki Omote

ORCID: 0000-0003-1210-1768
Publications
Citations
Views
---
Saved
---
About
Contact & Profiles
Research Areas
  • Fluorine in Organic Chemistry
  • Chemical Synthesis and Analysis
  • Synthesis and Reactions of Organic Compounds
  • Cyclopropane Reaction Mechanisms
  • Asymmetric Synthesis and Catalysis
  • Porphyrin and Phthalocyanine Chemistry
  • Synthesis of β-Lactam Compounds
  • Synthesis and Catalytic Reactions
  • Asymmetric Hydrogenation and Catalysis
  • X-ray Diffraction in Crystallography
  • Axial and Atropisomeric Chirality Synthesis
  • Crystallization and Solubility Studies
  • Catalytic C–H Functionalization Methods
  • Synthesis and Biological Evaluation
  • Carbohydrate Chemistry and Synthesis
  • Catalytic Cross-Coupling Reactions
  • Porphyrin Metabolism and Disorders
  • Photodynamic Therapy Research Studies
  • Inorganic Fluorides and Related Compounds
  • Molecular spectroscopy and chirality
  • Synthetic Organic Chemistry Methods
  • Chemical Synthesis and Reactions
  • Analytical Chemistry and Chromatography
  • Genetics, Aging, and Longevity in Model Organisms
  • Alkaloids: synthesis and pharmacology

Setsunan University
2015-2024

Electronic Systems Design (Malta)
2024

Soochow University
2020

Slovak University of Technology in Bratislava
2020

Jiangxi Provincial People's Hospital
2020

University of Minnesota
2020

Institute of Chemical Technology
2020

Universidade Federal do Rio de Janeiro
2020

Municipal Hirakata City Hospital
2015-2018

Albany State University
2005

A highly reactive alkylrhodium complex was formed from Me2Zn and RhCl(PPh3)3 effectively catalyzed a Csp3–Csp3 homocoupling reaction of benzyl halides. coupling using Rh catalyst has not been reported up to now. The proceeded under very mild conditions gave the corresponding products even if they had substituents such as an uncovered formyl or hydroxymethyl group.

10.1021/ol501619w article EN Organic Letters 2014-06-30

Synthesis of α-CF3 carbonyl compounds has been recognized to be difficult up now because the polarization CF3δ−-Iδ+ is opposite that CH3δ+-Iδ−, and this makes it introduce CF3+ unit enolates. We recently reported an effective α-trifluoromethylation ketones by using Et2Zn with Rh catalyst, but mechanism not fully cleared. Now, we carried out detailed mechanistic studies found involvement a highly reactive alkylrhodium complex which derived from RhCl(PPh3)3 in α-trifluoromethylation....

10.1021/jo9004348 article EN The Journal of Organic Chemistry 2009-04-14

(E)-Trimethyl-(3,3,3-trifluoroprop-1-enyl)silane (1) was synthesized as a reagent for use in Hiyama cross-coupling reactions the production of β-trifluoromethylstyrene derivatives. Cross-coupling 1 with electronically diverse aryl iodides achieved by treatment CsF presence catalytic amounts palladium to afford desired products moderate good yields.

10.1021/ol300670n article EN Organic Letters 2012-04-18

A nickel-catalyzed Negishi coupling of bromodifluoroacetamides with arylzinc reagents has been developed. This reaction allows access to difluoromethylated aromatic compounds containing a variety aryl groups and amide moieties. Furthermore, highly effective transformation the functionalized difluoromethyl group (−CF2CONR1R2) was realized via microwave-assisted reduction under mild conditions. The notable features this strategy are its generality use low-cost nickel catalyst ligand; thus,...

10.1021/acs.orglett.6b00232 article EN Organic Letters 2016-02-24

Abstract This account concentrates on our new methodologies for the synthesis of fluorine analogues amino acids and their derivatives using Reformatsky‐type reactions ethyl bromodifluoroacetate dibromofluoroacetate with imines promoted by Wilkinson catalyst. First, we present rhodium‐catalyzed reaction diethylzinc chemoselective α,α‐difluoro‐β‐lactams non‐cyclized products, 3‐alkylamino‐2,2‐difluorocarboxylates. was expanded to asymmetric difluoro‐β‐lactams two types chiral auxiliaries. To...

10.1002/adsc.201000506 article EN Advanced Synthesis & Catalysis 2010-10-26

An enantioselective Reformatsky reaction has been developed for the of ethyl dibromofluoroacetate (1) with an imine. This method represents first ligand-promoted imino-Reformatsky approach to use a halofluoroacetate. The amino alcohol ligand allowed preparation enantioenriched α-bromo-α-fluoro-β-lactams in good yields enantioselectivities up 96% ee. process also provided access β-lactam rings bearing two stereogenic centers.

10.1021/ol500631j article EN Organic Letters 2014-04-03

Treatment of alpha,beta-unsaturated ketones with CF(3)I in the presence Et(2)Zn and RhCl(PPh(3))(3) gave novel alpha-trifluoromethylation products good yields. Hydrogen transfer from ethyl group on rhodium complex to beta-position enone seems play an important role this reaction.

10.1021/ol048134v article EN Organic Letters 2004-10-20

A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on addition dimethylzinc to aldehydes. This will be useful for synthesis bioactive compounds with a methyl carbinol moiety. It could recycled without using solvent or column.

10.1021/ol070466n article EN Organic Letters 2007-04-11

1,3-Diketones were synthesized from α,β-unsaturated ketones by treatment with acid chlorides and Et2Zn in the presence of RhCl(PPh3)3. This is a very simple extremely chemoselective reaction to give adduct at α-position ketones.

10.1021/ol800660y article EN Organic Letters 2008-05-14

The photochemical properties of a coumarin derivative with promising electron-withdrawing fluoroalkyl group at the 3-position in solution and crystal were investigated detail.

10.1039/d4me00006d article EN Molecular Systems Design & Engineering 2024-01-01

Ethyl bromodifluoroacetate reacted with alkenyl or aryl iodides in the presence of copper powder dimethyl sulfoxide (DMSO) to give corresponding alkynyl- aryldiffuoroacetates moderated good yields.

10.1248/cpb.47.1013 article EN Chemical and Pharmaceutical Bulletin 1999-01-01

Catalytic Mannich reactions of 1,1-difluoro-2-trialkyl(aryl)silyl-2-trimethylsilyloxyethenes (3) with a variety sulfonylimines were utilized for the preparation α,α-difluoro-β-amino acid derivatives (7). The influence Lewis on reaction was examined. Methods conversion α,α-difluoroacylsilanes to α,α-difluorocarboxylic acids also explored.

10.1021/jo050953l article EN The Journal of Organic Chemistry 2005-08-19

The combination of Et2Zn and RhCl(PPh3)3 led to the facile generation a rhodium-hydride complex (Rh-H) that catalyzed 1,4-reduction α,β-unsaturated esters. resulting rhodium enolate performed as Reformatsky-type reagent reacted with various imines give syn-β-lactams in good excellent yields high diastereoselectivity.

10.1021/acs.joc.5b01233 article EN The Journal of Organic Chemistry 2015-07-23

Oxidative Sonogashira cross-coupling reactions of (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane with arylacetylene were achieved using silver fluoride and a palladium catalyst, to afford high yields various 1,3-enynes CF3 group on the terminal sp(2) carbon. Silver promoted C-Si bond dissociation oxidation palladium, enabling catalytic use palladium.

10.1039/c5ob01290b article EN Organic & Biomolecular Chemistry 2015-01-01

A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap commercially available amino alcohol ligand is described.

10.1039/c4ob01184h article EN Organic & Biomolecular Chemistry 2014-01-01
Coming Soon ...