Cooperative Rh(II)/Pd(0) Dual Catalysis: Synthesis of Highly Substituted 3(2H)-Furanones with a C2-Quaternary Center via a Cyclization/Allylic Alkylation Cascade of α-Diazo-δ-keto-esters

2021 ◽  
Author(s):  
Qian-Qian Zhou ◽  
Ming Cheng ◽  
Qing Liu ◽  
Bing-Qian Qu ◽  
Xiao-Yan Huang ◽  
...  
Keyword(s):  
Allylic Alkylation ◽  
Keto Esters ◽  
Quaternary Center ◽  
Dual Catalysis

Relay Rh(ii)/Pd(0) dual catalysis: synthesis of α-quaternary β-keto-esters via a [1,2]-sigmatropic rearrangement/allylic alkylation cascade of α-diazo tertiary alcohols

2020 ◽  
Vol 56 (5) ◽  
pp. 782-785 ◽  
Author(s):  
Xian-Xu Wang ◽  
Xiao-Yan Huang ◽  
Sen-Hao Lei ◽  
Fang Yang ◽  
Jin-Ming Gao ◽  
...  
Keyword(s):  
Palladium Catalysts ◽  
Sigmatropic Rearrangement ◽  
Allylic Alkylation ◽  
Tertiary Alcohols ◽  
Keto Esters ◽  
Dual Catalysis

Rhodium and palladium catalysts cooperated efficiently to promote domino [1,2]-sigmatropic rearrangement/allylic alkylation of α-diazo tertiary alcohols to access α-quaternary β-keto-esters.

scholarly journals Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

2013 ◽  
Vol 9 ◽  
pp. 1853-1857 ◽  
Author(s):  
Lin Yan ◽  
Zhiqiang Han ◽  
Bo Zhu ◽  
Caiyun Yang ◽  
Choon-Hong Tan ◽  
...  
Keyword(s):  
Fluorine Atom ◽  
Allylic Alkylation ◽  
Quaternary Carbon ◽  
Asymmetric Allylic Alkylation ◽  
Keto Esters

In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).

Stereoselective and Site-Specific Allylic Alkylation of Amino Acids and Small Peptides via a Pd/Cu Dual Catalysis

2017 ◽  
Vol 139 (29) ◽  
pp. 9819-9822 ◽  
Author(s):  
Xiaohong Huo ◽  
Rui He ◽  
Jingke Fu ◽  
Jiacheng Zhang ◽  
Guoqiang Yang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Allylic Alkylation ◽  
Small Peptides ◽  
Site Specific ◽  
Dual Catalysis

scholarly journals Enantioselective Total Synthesis of (–)-Myrifabral A and B

2020 ◽  
Author(s):  
Tyler J. Fulton ◽  
Anthony Chen ◽  
Michael Bartberger ◽  
Brian Stoltz
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Enantioselective Total Synthesis ◽  
Cross Metathesis ◽  
Quaternary Center ◽  
Tricyclic Core ◽  
Iminium Ion ◽  
Palladium Catalyzed

<p>A catalytic enantioselective approach to the myrioneuron alkaloids (–)-myrifabral A and (–)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (–)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (–)-myrifabral A to (–)-myrifabral B.</p>

Stereoselective Allylic Alkylation of 1-Pyrroline-5-carboxylic Esters via a Pd/Cu Dual Catalysis

2018 ◽  
Vol 20 (20) ◽  
pp. 6564-6568 ◽  
Author(s):  
Penglin Liu ◽  
Xiaohong Huo ◽  
Bowen Li ◽  
Rui He ◽  
Jiacheng Zhang ◽  
...  
Keyword(s):  
Allylic Alkylation ◽  
Dual Catalysis ◽  
Carboxylic Esters

Carbonyl-Photoredox/Metal Dual Catalysis: Applications in Organic Synthesis

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3493-3510
Author(s):  
Hong-Xi Li ◽  
Da-Liang Zhu ◽  
David James Young
Keyword(s):  
Bond Formation ◽  
Short Review ◽  
Hydrogen Atom Transfer ◽  
Aryl Halides ◽  
Single Electron Transfer ◽  
Carbonyl Complexes ◽  
Keto Esters ◽  
Aryl Bromides ◽  
Dual Catalysis ◽  
Transfer Agents

Photoredox/metal dual catalysis is a versatile tandem methodology to construct carbon–carbon and carbon–heteroatom bonds. The focus of this short review is the application of this technology to C(sp3)–C(sp3), C(sp3)–C(sp2), C(sp2)–C(sp2), C(sp2)–O, and C(sp3)–O bond formation induced by readily available and inexpensive carbonyl complexes as single electron transfer agents, photosensitizers, or hydrogen atom transfer agents.1 Introduction2 Homocoupling of Aryl Halides3 Functionalization of C(sp3)–H Bonds3.1 Dehydrogenation of Alkanes3.2 Arylation/Alkylation3.3 Carboxylation3.4 Acylation3.5 Hydroalkylation of Olefins3.6 Hydroalkylation of Imines4 Benzoylation of Aryl Bromides5 Aryl Esterification6 Oxidation of β-Keto Esters7 Conclusions and Future Outlook

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