Masanari Kimura

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Organization: Nagasaki University , Japan

Department: Graduate School of Engineering

Title: Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Copper-Catalyzed Stereodefined Construction of Acrylic Acid Derivatives from Terminal Alkynes via CO2 Insertion

Co-reporter:Kenta Kuge, Ying Luo, Yuki Fujita, Yasuyuki Mori, Gen Onodera, and Masanari Kimura

Organic Letters 2017 Volume 19(Issue 4) pp:

Publication Date(Web):February 8, 2017

DOI:10.1021/acs.orglett.6b03860

IPrCuCl catalyzes the CO2 insertion reaction undergone by a dialkylvinylborane intermediate derived from alkynyltrialkylborate by a 1,2-alkyl group migration to afford α-alkyl acrylic acids with excellent regio- and stereoselectivities.

Palladium-Catalyzed [4 + 2] Cycloaddition of Aldimines and 1,4-Dipolar Equivalents via Amphiphilic Allylation

Co-reporter:Goki Hirata, Naoshi Yamada, Shohei Sanada, Gen Onodera, and Masanari Kimura

Organic Letters 2015 Volume 17(Issue 3) pp:600-603

Publication Date(Web):January 28, 2015

DOI:10.1021/ol503614d

The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels–Alder reaction followed by an oxidation reaction with DDQ.

Efficient synthesis of pyrrolizidine by Pd-catalyzed consecutive double amphiphilic allylation of nitrile

Co-reporter:Naoshi Yamada, Goki Hirata, Gen Onodera, Masanari Kimura

Tetrahedron 2015 Volume 71(Issue 37) pp:6541-6546

Publication Date(Web):16 September 2015

DOI:10.1016/j.tet.2015.04.110

The combination of a Pd catalyst and triethylborane promotes double amphiphilic allylation of nitriles with 2-methylenepropane-1,3-diol to serve as a 1,3-dipolar equivalent, providing pyrrolizidine derivatives. The resulting bicyclic compounds can be used for efficient synthesis of important pyrrolizidine alkaloids.

C–C bond formation via 1,2-addition of a tert-butylzinc reagent and carbonyls across conjugated dienes

Co-reporter:Yuki Ohira, Maya Hayashi, Takamichi Mori, Gen Onodera and Masanari Kimura

New Journal of Chemistry 2014 vol. 38(Issue 1) pp:330-337

Publication Date(Web):19 Nov 2013

DOI:10.1039/C3NJ00992K

A mixture of t-butylzinc halide and an aldehyde reacts with conjugated dienes to provide 2-neopentyl homoallyl alcohols in high yields by 1,2-addition. Without the aldehyde, under carbon dioxide atmospheric pressure, the three components of t-butylzinc halide, butadiene, and carbon dioxide combine in a 1:1:1 ratio to give 2-neopentyl-3-butenoic acid in excellent yield.

Efficient and Selective Formation of Unsaturated Carboxylic and Phenylacetic Acids from Diketene

Co-reporter:Takamichi Mori;Yusuke Akioka;Hisaho Kawahara;Ryo Ninokata;Dr. Gen Onodera ;Dr. Masanari Kimura

Angewandte Chemie 2014 Volume 126( Issue 39) pp:10602-10606

Publication Date(Web):

DOI:10.1002/ange.201404816

Abstract

A nickel catalyst promotes the multicomponent coupling reaction of diketene, an alkyne, and Me₂Zn to provide 3-methylene-4-hexenoic acids in excellent yields. Under similar conditions, the combination of the nickel catalyst and Et₂Al(OEt) promotes a cycloaddition reaction involving dimerization of an alkyne to furnish phenylacetic acids. In the presence of PPh₃, a formal [2+2+1+1] cycloaddition reaction proceeds to afford regioisomeric phenylacetic acids via cleavage of the CC bond.

Efficient and Selective Formation of Unsaturated Carboxylic and Phenylacetic Acids from Diketene

Co-reporter:Takamichi Mori;Yusuke Akioka;Hisaho Kawahara;Ryo Ninokata;Dr. Gen Onodera ;Dr. Masanari Kimura

Angewandte Chemie International Edition 2014 Volume 53( Issue 39) pp:10434-10438

Publication Date(Web):

DOI:10.1002/anie.201404816

Abstract

Stereodefined Construction of Trisubstituted Alkenes by Direct Coupling Reaction of Allylating Agents, Alkynes, and Organoboranes

Co-reporter:Masahiro Fukushima;Daiki Takushima;Hideaki Satomura;Dr. Gen Onodera ; Dr. Masanari Kimura

Chemistry - A European Journal 2012 Volume 18( Issue 26) pp:8019-8023

Publication Date(Web):

DOI:10.1002/chem.201201138

Stereoselective Coupling Reaction of Dimethylzinc and Alkyne toward Nickelacycles

Co-reporter:Takamichi Mori, Toshiyuki Nakamura, and Masanari Kimura

Organic Letters 2011 Volume 13(Issue 9) pp:2266-2269

Publication Date(Web):March 30, 2011

DOI:10.1021/ol2005352

Ni catalyst promotes the three-component coupling reaction of vinyloxacyclopropane, alkyne, and dimethylzinc to provide 2,5-heptadienyl alcohol in high yields. Vinylcyclopropane also participates in a similar three-component coupling reaction to afford dimethyl (α-heptadienyl)malonate with excellent E-stereoselectivity.

Nucleophilic allylation of N,O-acetals with allylic alcohols promoted by Pd/Et3B and Pd/Et2Zn systems

Co-reporter:Yumi Yamaguchi, Mariko Hashimoto, Katsumi Tohyama, Masanari Kimura

Tetrahedron Letters 2011 Volume 52(Issue 8) pp:913-915

Publication Date(Web):23 February 2011

DOI:10.1016/j.tetlet.2010.12.064

Pd/Et3B and Pd/Et2Zn systems promote the nucleophilic allylations of 2-aminotetrahydrofuran and 2-aminotetrahydropyran with allylic alcohols to provide ω-hydroxyhomoallylamines in high yields. The transformation is applicable to the allylation of non-protective carbohydrates, such as ribose and deoxyribose.

Dienyl Homoallyl Alcohols via Palladium Catalyzed Ene-Type Reaction of Aldehydes with 1,3-Dienes

Co-reporter:Masahiro Fukushima ; Daiki Takushima

Journal of the American Chemical Society 2010 Volume 132(Issue 46) pp:16346-16348

Publication Date(Web):October 28, 2010

DOI:10.1021/ja1072417

The combination of Pd catalyst and Xantphos ligand in the presence of Et3B nicely promotes the allylation of aldehydes with conjugated dienes to provide dienyl homoallyl alcohols in excellent yields. The reaction occurs selectively at the C−C double bond bearing higher electron density.

Rh-Catalyzed Reductive Coupling Reaction of Aldehydes with Conjugated Dienes Promoted by Triethylborane

Co-reporter:Masanari Kimura, Daisuke Nojiri, Masahiro Fukushima, Shuichi Oi, Yusuke Sonoda and Yoshio Inoue

Organic Letters 2009 Volume 11(Issue 17) pp:3794-3797

Publication Date(Web):August 7, 2009

DOI:10.1021/ol901527b

Rh(I) catalyzes the reductive coupling reaction of a wide variety of aldehydes with conjugated dienes in the presence of a stoichiometric amount of triethylborane to provide homoallyl alcohols in a single operation.

Nickel-catalyzed multi-component coupling reaction of aldimine, alkyne, and dimethylzinc via dimerization of butadiene

Co-reporter:Masanari Kimura, Mariko Togawa, Yasushi Tatsuyama, Kimiko Matsufuji

Tetrahedron Letters 2009 50(27) pp: 3982-3984

Publication Date(Web):

DOI:10.1016/j.tetlet.2009.04.086

Convenient Synthesis of Pyrrolidines by Amphiphilic Allylation of Imines with 2-Methylenepropane-1,3-diols

Co-reporter:Masanari Kimura Dr.;Takato Tamaki;Masanori Nakata;Katsumi Tohyama ;Yoshinao Tamaru Dr.

Angewandte Chemie 2008 Volume 120( Issue 31) pp:5887-5889

Publication Date(Web):

DOI:10.1002/ange.200801252

Convenient Synthesis of Pyrrolidines by Amphiphilic Allylation of Imines with 2-Methylenepropane-1,3-diols

Co-reporter:Masanari Kimura Dr.;Takato Tamaki;Masanori Nakata;Katsumi Tohyama ;Yoshinao Tamaru Dr.