Mechanistic Insight into Asymmetric Hetero-Michael Addition of α,β-Unsaturated Carboxylic Acids Catalyzed by Multifunctional Thioureas

Noboru Hayama; Ryuta Kuramoto; Tamás Földes; Kazuya Nishibayashi; Yusuke Kobayashi; Imre Pápai; Yoshiji Takemoto

doi:10.1021/jacs.8b07511

Mechanistic Insight into Asymmetric Hetero-Michael Addition of α,β-Unsaturated Carboxylic Acids Catalyzed by Multifunctional Thioureas

Journal of the American Chemical Society ◽

10.1021/jacs.8b07511 ◽

2018 ◽

Vol 140 (38) ◽

pp. 12216-12225 ◽

Cited By ~ 24

Author(s):

Noboru Hayama ◽

Ryuta Kuramoto ◽

Tamás Földes ◽

Kazuya Nishibayashi ◽

Yusuke Kobayashi ◽

...

Keyword(s):

Carboxylic Acids ◽

Michael Addition ◽

Mechanistic Insight ◽

Unsaturated Carboxylic Acids ◽

Insight Into

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A solvent-dependent chirality-switchable thia-Michael addition to α,β-unsaturated carboxylic acids using a chiral multifunctional thiourea catalyst

Chemical Science ◽

10.1039/d0sc01729a ◽

2020 ◽

Vol 11 (21) ◽

pp. 5572-5576 ◽

Cited By ~ 1

Author(s):

Noboru Hayama ◽

Yusuke Kobayashi ◽

Eriko Sekimoto ◽

Anna Miyazaki ◽

Kiyofumi Inamoto ◽

...

Keyword(s):

Carboxylic Acids ◽

Tertiary Amine ◽

Michael Addition ◽

Arylboronic Acid ◽

Unsaturated Carboxylic Acids

An asymmetric thia-Michael addition of arylthiols to α,β-unsaturated carboxylic acids using a thiourea catalyst that bears arylboronic acid and tertiary amine moieties is reported.

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Quantum chemical investigation on the reaction mechanism of tertiary phosphines with unsaturated carboxylic acids: An insight into kinetic data

International Journal of Quantum Chemistry ◽

10.1002/qua.24161 ◽

2012 ◽

Vol 113 (8) ◽

pp. 1086-1094 ◽

Cited By ~ 14

Author(s):

Alexey V. Salin ◽

Roza M. Aminova ◽

Vladimir I. Galkin

Keyword(s):

Reaction Mechanism ◽

Carboxylic Acids ◽

Quantum Chemical ◽

Kinetic Data ◽

Chemical Investigation ◽

Quantum Chemical Investigation ◽

Tertiary Phosphines ◽

Unsaturated Carboxylic Acids ◽

Insight Into

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ChemInform Abstract: Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids.

ChemInform ◽

10.1002/chin.201645066 ◽

2016 ◽

Vol 47 (45) ◽

Author(s):

Noboru Hayama ◽

Takumi Azuma ◽

Yusuke Kobayashi ◽

Yoshiji Takemoto

Keyword(s):

Carboxylic Acids ◽

Michael Addition ◽

Arylboronic Acid ◽

Unsaturated Carboxylic Acids

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Transition-Metal-Free and Chemoselective NaOtBu–O2-Mediated Oxidative Cleavage Reactions of vic-1,2-Diols to Carboxylic Acids and Mechanistic Insight into the Reaction Pathways

Organic Letters ◽

10.1021/ol501012f ◽

2014 ◽

Vol 16 (11) ◽

pp. 2876-2879 ◽

Cited By ~ 19

Author(s):

Sun Min Kim ◽

Dong Wan Kim ◽

Jung Woon Yang

Keyword(s):

Transition Metal ◽

Carboxylic Acids ◽

Oxidative Cleavage ◽

Reaction Pathways ◽

Metal Free ◽

Mechanistic Insight ◽

Cleavage Reactions ◽

Insight Into

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ChemInform Abstract: Transition-Metal-Free and Chemoselective NaOtBu-O2-Mediated Oxidative Cleavage Reactions of vic-1,2-Diols to Carboxylic Acids and Mechanistic Insight into the Reaction Pathways.

ChemInform ◽

10.1002/chin.201447072 ◽

2014 ◽

Vol 45 (47) ◽

pp. no-no

Author(s):

Sun Min Kim ◽

Dong Wan Kim ◽

Jung Woon Yang

Keyword(s):

Transition Metal ◽

Carboxylic Acids ◽

Oxidative Cleavage ◽

Reaction Pathways ◽

Metal Free ◽

Mechanistic Insight ◽

Cleavage Reactions ◽

Insight Into

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Novel Aza‐Michael Addition‐Asymmetric Protonation to α,β‐Unsaturated Carboxylic Acids with Chiral Thiourea‐Boronic Acid Hybrid Catalysts

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.202100145 ◽

2021 ◽

Author(s):

Hiroki Murakami ◽

Ayano Yamada ◽

Kenichi Michigami ◽

Yoshiji Takemoto

Keyword(s):

Carboxylic Acids ◽

Michael Addition ◽

Boronic Acid ◽

Hybrid Catalysts ◽

Unsaturated Carboxylic Acids

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ChemInform Abstract: Dienediolates from Unsaturated Carboxylic Acids: Michael Addition of Dilithium Buta-1,3-diene-1,1-diolate (from Crotonic Acid) to Unsaturated Ketones.

ChemInform ◽

10.1002/chin.198843083 ◽

1988 ◽

Vol 19 (43) ◽

Author(s):

P. BALLESTER ◽

A. COSTA ◽

A. GARCIA-RASO ◽

A. GOMEZ-SOLIVELLAS ◽

R. MESTRES

Keyword(s):

Carboxylic Acids ◽

Michael Addition ◽

Crotonic Acid ◽

Unsaturated Ketones ◽

Unsaturated Carboxylic Acids

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Dienediolates from unsaturated carboxylic acids: Michael addition of dilithium buta-1,3-diene-1,1-diolate (from crotonic acid) to unsaturated ketones

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19880001711 ◽

1988 ◽

pp. 1711-1717 ◽

Cited By ~ 13

Author(s):

Pablo Ballester ◽

Antonio Costa ◽

Angel Garcia Raso ◽

Antonio Gómez-Solivellas ◽

Ramon Mestres

Keyword(s):

Carboxylic Acids ◽

Michael Addition ◽

Crotonic Acid ◽

Unsaturated Ketones ◽

Unsaturated Carboxylic Acids

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Mechanistic Insight into Fast and Highly Efficient Organocatalytic Activity of a Tripodal Dimeric Hexaurea Capsular Assembly in Michael Addition Reactions

ACS Omega ◽

10.1021/acsomega.8b01780 ◽

2018 ◽

Vol 3 (9) ◽

pp. 10647-10656

Author(s):

Tamal Kanti Ghosh ◽

Rajib Ghosh ◽

Pradyut Ghosh

Keyword(s):

Michael Addition ◽

Addition Reactions ◽

Highly Efficient ◽

Mechanistic Insight ◽

Insight Into

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Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.c15-00983 ◽

2016 ◽

Vol 64 (7) ◽

pp. 704-717 ◽

Cited By ~ 15

Author(s):

Noboru Hayama ◽

Takumi Azuma ◽

Yusuke Kobayashi ◽

Yoshiji Takemoto

Keyword(s):

Carboxylic Acids ◽

Michael Addition ◽

Arylboronic Acid ◽

Unsaturated Carboxylic Acids

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