ChemInform Abstract: THIOL ESTERS IN ORGANIC SYNTHESIS. X. A NEW APPROACH TO 1,5-KETOLS AND 5-HYDROXY ESTERS USING S,S′-DIETHYL DITHIOMALONATE AS AN ETHANOL CARBANION EQUIVALENT

1982 ◽  
Vol 13 (20) ◽  
Author(s):  
H.-J. LIU ◽  
I. V. OPPONG
Keyword(s):  
Organic Synthesis ◽  
New Approach ◽  
Thiol Esters ◽  
Hydroxy Esters

Thiol esters in organic synthesis. X. A new approach to 1,5-ketols and 5-hydroxy esters using S,S'-diethyl dithiomalonate as an ethanol carbanion equivalent

1982 ◽  
Vol 60 (1) ◽  
pp. 94-96 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Isaac V. Oppong
Keyword(s):  
Organic Synthesis ◽  
Raney Nickel ◽  
Michael Addition ◽  
New Approach ◽  
Unsaturated Esters ◽  
Thiol Esters ◽  
Hydroxy Esters

Michael addition of S,S′-diethyl dithiomalonate to conjugated enones and α,β-unsaturated esters followed by reduction with Raney nickel gave rise to 1,5-ketols and 5-hydroxy esters respectively in good yields.

scholarly journals Learning from B12 enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

2018 ◽  
Vol 14 ◽  
pp. 2553-2567 ◽  
Author(s):  
Keishiro Tahara ◽  
Ling Pan ◽  
Toshikazu Ono ◽  
Yoshio Hisaeda
Keyword(s):  
Organic Synthesis ◽  
Reaction Mechanisms ◽  
Catalytic Reactions ◽  
Vitamin B ◽  
Catalytic Systems ◽  
New Approach ◽  
Enzyme Functions

Cobalamins (B12) play various important roles in vivo. Most B12-dependent enzymes are divided into three main subfamilies: adenosylcobalamin-dependent isomerases, methylcobalamin-dependent methyltransferases, and dehalogenases. Mimicking these B12 enzyme functions under non-enzymatic conditions offers good understanding of their elaborate reaction mechanisms. Furthermore, bio-inspiration offers a new approach to catalytic design for green and eco-friendly molecular transformations. As part of a study based on vitamin B12 derivatives including heptamethyl cobyrinate perchlorate, we describe biomimetic and bioinspired catalytic reactions with B12 enzyme functions. The reactions are classified according to the corresponding three B12 enzyme subfamilies, with a focus on our recent development on electrochemical and photochemical catalytic systems. Other important reactions are also described, with a focus on radical-involved reactions in terms of organic synthesis.

Thiol esters in organic synthesis. XVI. Formation of α,β-unsaturated thiol esters via a Wadsworth–Emmons process

1991 ◽  
Vol 69 (6) ◽  
pp. 934-936 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Patricia A. Rose ◽  
Doug J. Sasaki
Keyword(s):  
Key Words ◽  
Organic Synthesis ◽  
Thiol Esters ◽  
Wittig Reagent

α,β-Unsaturated thiol esters could be readily prepared via a Wadsworth–Emmons reaction using diethyl alkylthiocarbonylmethylphosphonate, which proved to be superior in reactivity to the corresponding Wittig reagent. Key words: α,β-unsaturated thiol esters, Wadsworth–Emmons reaction.

scholarly journals Metal-Free Aryl Cross-Coupling Directed by Traceless Linkers

2019 ◽  
Author(s):  
Veit G. Haensch ◽  
Toni Neuwirth ◽  
Johannes Steinmetzer ◽  
Florian Kloss ◽  
Rainer Beckert ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Quantum Chemical ◽  
Singlet State ◽  
Cross Coupling ◽  
Excited Singlet ◽  
Reaction Conditions ◽  
Photochemical Process ◽  
New Approach ◽  
Metal Free ◽  
Membered Transition State

<div>The metal-free, highly selective synthesis of biaryls poses a major challenge in organic synthesis. We report the scope and mechanism of a promising new approach to (hetero)biaryls by the photochemical fusion of aryl substituents tethered to a traceless linker (photosplicing). Interrogating photosplicing with varying reaction conditions and comparison of diverse synthetic probes (40 examples, including a suite of heterocycles) showed that the reaction has a surprisingly broad scope and involves neither metals nor radicals. Quantum chemical calculations revealed that the C–C bond is formed by an intramolecular photochemical process that involves an excited singlet state and the traverse of a five-membered transition state, thus warranting consistent <i>ipso</i>‑<i>ipso</i>‑coupling fidelity. These results demonstrate that photosplicing is a unique aryl cross-coupling method in the excited state that can be applied to synthesize a broad range of biaryls. </div>

Thiol esters in organic synthesis. XIV. The total synthesis of racemic α-costal

1986 ◽  
Vol 64 (4) ◽  
pp. 658-666 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Hla Wynn
Keyword(s):  
Total Synthesis ◽  
Organic Synthesis ◽  
Salient Feature ◽  
Tert Butyl ◽  
Racemic Form ◽  
Thiol Esters

The first total synthesis of α-costal (1) in racemic form has been achieved in an unequivocal manner whereby the structure previously assigned to the natural aldehyde is confirmed. A salient feature of the synthesis is the use of S-tert-butyl cyanothiolacetate to facilitate the introduction of the labile acrolein unit.

Zwitterionic Metal-Enolate or Equivalent: Generation and Capture

Synlett ◽  
2022 ◽  
Author(s):  
Linhong Zuo ◽  
Wusheng Guo
Keyword(s):  
Organic Synthesis ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
New Approach ◽  
Material Chemistry

Functionalized ketones and their derivatives are very important building blocks in organic synthesis and material chemistry. The development of novel methodology for the chemo-, regio-, diastereo-, stereo- and enantioselective synthesis of functionalized ketones and their derivatives is the continuous endeavor of organic chemists. Herein we highlight the new approach that was recently initiated and developed by our group for the synthesis of (enantioenriched) ketones and related derivatives based on zwitterionic metal-enolate (ZME) chemistry.

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