Squaramide-Catalyzed Enantioselective Michael Addition of Pyrazol-3- ones to ortho-Quinone Methides

Laura Carceller-Ferrer; Gonzalo Blay; José R. Pedro; Carlos Vila

doi:10.2174/1876402911666190806105543

Squaramide-Catalyzed Enantioselective Michael Addition of Pyrazol-3- ones to ortho-Quinone Methides

Letters in Organic Chemistry ◽

10.2174/1876402911666190806105543 ◽

2020 ◽

Vol 17 (11) ◽

pp. 837-844

Author(s):

Laura Carceller-Ferrer ◽

Gonzalo Blay ◽

José R. Pedro ◽

Carlos Vila

Keyword(s):

Michael Addition ◽

Enantiomeric Excess ◽

Quinone Methides

A bifunctional squaramide catalyzed the enantioselective Michael addition of pyrazol-3- ones to ortho-quinone methides, generated in situ from 2-(1-tosylalkyl)phenols is presented. The corresponding chiral pyrazolones are obtained with good to excellent yields (27-98%) and enantiomeric excess (14-99% ee).

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Metal-Free One-Pot Synthesis of 3-Phosphinoylbenzofurans via Phospha-Michael Addition/Cyclization of H-Phosphine Oxides and in Situ Generated ortho-Quinone Methides

Organic Letters ◽

10.1021/acs.orglett.7b03863 ◽

2018 ◽

Vol 20 (2) ◽

pp. 477-480 ◽

Cited By ~ 34

Author(s):

Ji-Yuan Du ◽

Yan-Hua Ma ◽

Rui-Qing Yuan ◽

Nana Xin ◽

Shao-Zhen Nie ◽

...

Keyword(s):

Michael Addition ◽

Phosphine Oxides ◽

Quinone Methides ◽

One Pot ◽

Metal Free ◽

One Pot Synthesis

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An organic-base catalyzed asymmetric 1,4-addition of tritylthiol to in situ generated aza-o-quinone methides at the H2O/DCM interface

Chemical Communications ◽

10.1039/c8cc09382b ◽

2019 ◽

Vol 55 (18) ◽

pp. 2668-2671 ◽

Cited By ~ 4

Author(s):

Xianghui Liu ◽

Kai Wang ◽

Wengang Guo ◽

Yan Liu ◽

Can Li

Keyword(s):

Michael Addition ◽

Organic Base ◽

Quinone Methides

Highly enantioselective organocatalytic Michael addition of tritylthiol to N-o-QM intermediates generated in situ at the H2O/DCM interface is presented.

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Relay Cu(I)/Brønsted Base Catalysis for Phospha ‐Michael Addition/5‐ exo ‐ dig Cyclization/Isomerization of in situ Formed aza ‐Alkynyl o‐ quinone methides with P(O)−H compounds to C3‐Phosphorylated Indoles

Advanced Synthesis & Catalysis ◽

10.1002/adsc.202100275 ◽

2021 ◽

Author(s):

Long Chen ◽

Xiao‐Yan Liu ◽

Jing Zhang ◽

Li Duan ◽

Zhong Wen ◽

...

Keyword(s):

Michael Addition ◽

Base Catalysis ◽

Quinone Methides ◽

Brønsted Base

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Scandium(III)-Catalyzed Aza-Michael Addition of in Situ Generated ortho-Quinone Methides with Amines: An Efficient Access to Betti Base Derivatives

Chinese Journal of Organic Chemistry ◽

10.6023/cjoc201808045 ◽

2019 ◽

Vol 39 (3) ◽

pp. 709

Author(s):

Shuo Zhang ◽

Ning Zhao ◽

Qinggang Li ◽

Jiaqi Zhang ◽

Zitong Hou ◽

...

Keyword(s):

Michael Addition ◽

Quinone Methides ◽

Betti Base ◽

Efficient Access

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Organocatalytic Enantioselective 1,6-aza -Michael Addition of Isoxazolin-5-ones to p -Quinone Methides

European Journal of Organic Chemistry ◽

10.1002/ejoc.201901907 ◽

2020 ◽

Vol 2020 (5) ◽

pp. 627-630 ◽

Cited By ~ 6

Author(s):

Ricardo Torán ◽

Carlos Vila ◽

Amparo Sanz-Marco ◽

M. Carmen Muñoz ◽

José R. Pedro ◽

...

Keyword(s):

Michael Addition ◽

Quinone Methides

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ChemInform Abstract: Facile Synthesis of 3-sec-Alkyl Substituted 7-Azaindoles by Michael Addition of Carbon Nucleophiles to Vinylogous Imine Intermediates Generated in situ from 3-(1-Arylsulfonylalkyl)-7-azaindoles.

ChemInform ◽

10.1002/chin.201531066 ◽

2015 ◽

Vol 46 (31) ◽

pp. no-no

Author(s):

Gan Luo ◽

Linhai Jing ◽

Dabin Qin ◽

Rongming Wang ◽

Lunqiang Jin ◽

...

Keyword(s):

Michael Addition ◽

Facile Synthesis ◽

Carbon Nucleophiles

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ent-Kaurane Diterpenoids from Chinese Liverworts and Their Antitumor Activities through Michael Addition As Detected in Situ by a Fluorescence Probe

Journal of Medicinal Chemistry ◽

10.1021/acs.jmedchem.5b00208 ◽

2015 ◽

Vol 58 (9) ◽

pp. 3944-3956 ◽

Cited By ~ 47

Author(s):

Zhaomin Lin ◽

Yanxia Guo ◽

Yanhui Gao ◽

Shuqi Wang ◽

Xiaoning Wang ◽

...

Keyword(s):

Michael Addition ◽

Fluorescence Probe ◽

Antitumor Activities

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Cinchona Alkaloid Catalyzed Enantioselective [4 + 2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans

The Journal of Organic Chemistry ◽

10.1021/acs.joc.7b00370 ◽

2017 ◽

Vol 82 (10) ◽

pp. 5433-5440 ◽

Cited By ~ 33

Author(s):

Yu-Hua Deng ◽

Wen-Dao Chu ◽

Xiang-Zhi Zhang ◽

Xu Yan ◽

Ke-Yin Yu ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Cinchona Alkaloid ◽

Quinone Methides ◽

Allenic Esters

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Catalytic enantioselective Michael addition reactions between in situ detrifluoroacetylatively generated 3-fluorooxindole-derived enolates and 1-(1-(phenylsulfonyl)vinylsulfonyl)benzene

Journal of Fluorine Chemistry ◽

10.1016/j.jfluchem.2018.12.009 ◽

2019 ◽

Vol 219 ◽

pp. 32-38 ◽

Cited By ~ 4

Author(s):

Yi Zhu ◽

YiFan Ni ◽

Vadim A. Soloshonok ◽

Jianlin Han ◽

Yi Pan

Keyword(s):

Michael Addition ◽

Addition Reactions

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Lewis acid-catalyzed tandem cyclization of in situ generated o-quinone methides and arylsulfonyl hydrazides for a one-pot entry to 3-sulfonylbenzofurans

Organic Chemistry Frontiers ◽

10.1039/c9qo01196j ◽

2019 ◽

Vol 6 (24) ◽

pp. 3929-3933 ◽

Cited By ~ 2

Author(s):

Fan-Xiao Meng ◽

Ruo-Nan Wang ◽

Hong-Li Huang ◽

Shu-Wen Gong ◽

Qian-Li Li ◽

...

Keyword(s):

Lewis Acid ◽

Quinone Methides ◽

One Pot ◽

Acid Catalyzed ◽

Tandem Cyclization ◽

First Time

Lewis acid-mediated one-pot tandem cyclization of o-QMs with arylsulfonyl hydrazides was described for the first time and the corresponding 3-sulfonylbenzofuran products were obtained in moderate to good yields.

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