Stereoselective synthesis of (Z)-1,3-bis(α,β-unsaturated carbonyl)-isoindolines from aldehydes and phenacyl azides under metal free conditions

2021 ◽  
Vol 57 (75) ◽  
pp. 9542-9545
Author(s):  
Budaganaboyina Prasad ◽  
Mandalaparthi Phanindrudu ◽  
Jagadeesh Babu Nanubolu ◽  
Ahmed Kamal ◽  
Dharmendra Kumar Tiwari
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free

We report herein our observation of an unprecedented stereoselective synthesis of 2H-isoindolin-1,3-ylidenes from 2-formylphenyl acrylates and phenacylazide in the presence of piperidine.

A Metal-free and β-Stereoselective Synthesis of 2-Deoxy-C-aryl Glycosides: Synthesis of 5-aza analogues of Aquayamycin

Synlett ◽  
2021 ◽  
Author(s):  
Yuling Mei ◽  
nan jiang ◽  
Yu Yang ◽  
Wan Zhang ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free ◽  
Wide Range ◽  
One Step ◽  
Aryl Glycosides ◽  
Aryl Glycoside

A convenient protocol for β-stereoselective synthesis of 2-deoxy-C-aryl glycosides has been developed. This reaction takes place in one step by using I2/Et3SiH to activate glycosyl acetate to generate glycosyl iodide intermediate in situ, which was captured by naphthol followed by Fries-like O- → C-glycoside rearrangement to selectively afford β-C-aryl glycoside. The approach is applicable to a wide range of naphthol modules, and its utility was demonstrated in the synthesis of 5-aza analogues of Aquayamycin.

scholarly journals Evaluation of In-Batch and In-Flow Synthetic Strategies towards the Stereoselective Synthesis of a Fluorinated Analogue of Retro-Thiorphan

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2260
Author(s):  
Margherita Pirola ◽  
Alessandra Puglisi ◽  
Laura Raimondi ◽  
Alessandra Forni ◽  
Maurizio Benaglia
Keyword(s):  
Continuous Flow ◽  
Stereoselective Synthesis ◽  
Catalytic Reduction ◽  
Lewis Base ◽  
Crucial Point ◽  
X Ray ◽  
Metal Free ◽  
Target Molecule ◽  
Synthetic Strategy ◽  
Synthetic Sequence

A stereoselective synthetic strategy for the preparation of trifluoromethylamine mimics of retro-thiorphan, involving a diastereoselective, metal-free catalytic step, has been studied in batch and afforded the target molecule in good yields and high diastereoselectivity. A crucial point of the synthetic sequence was the catalytic reduction of a fluorinated enamine with trichlorosilane as reducing agent in the presence of a chiral Lewis base. The absolute configuration of the key intermediate was unambiguously assigned by X-ray analysis. The synthesis was also investigated exploiting continuous flow reactions; that is, an advanced intermediate of the target molecule was synthesized in only two in-flow synthetic modules, avoiding isolation and purifications of intermediates, leading to the isolation of the target chiral fluorinated amine in up to an 87:13 diastereoisomeric ratio.

Metal‐Free Radical Annulation‐Hydrofunctionalization of 1,6‐Enynes for Stereoselective Synthesis of ( E )‐1‐Indanones

2020 ◽  
Vol 9 (7) ◽  
pp. 1040-1044 ◽  
Author(s):  
Ya‐Nan Wu ◽  
Tian‐Shu Zhang ◽  
Wen‐Juan Hao ◽  
Shu‐Jiang Tu ◽  
Bo Jiang
Keyword(s):  
Free Radical ◽  
Stereoselective Synthesis ◽  
Metal Free

scholarly journals One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3594 ◽  
Author(s):  
Muzalevskiy ◽  
Sizova ◽  
Belyaeva ◽  
Trofimov ◽  
Nenajdenko
Keyword(s):  
Stereoselective Synthesis ◽  
One Pot ◽  
Metal Free

The reaction of pyridines with trifluoroacetylated acetylenes was investigated. It was found that the reaction of various pyridines with two molecules of CF3CO-acetylenes proceeds under mild metal-free conditions. As a result, efficient stereoselective synthesis of 3-arylethynyl-3-trifluoromethyl-1,3-oxazinopyridines was elaborated. Target heterocycles can be prepared in up to quantitative yields.

Highly stereoselective synthesis of 1-cyanocyclopropane-carboxamides from 3-substituted-2-cyanoacrylamides with N -tosylhydrazones under metal-free conditions

2017 ◽  
Vol 58 (31) ◽  
pp. 3003-3007 ◽  
Author(s):  
Xufeng Nie ◽  
Yachuan Wang ◽  
Lijun Yang ◽  
Zaijun Yang ◽  
Tairan Kang
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free

scholarly journals Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement

2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Bo Zhou ◽  
Ying-Qi Zhang ◽  
Kairui Zhang ◽  
Ming-Yang Yang ◽  
Yang-Bo Chen ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Metal Free

Metal-free enaminone C-N bond cyanation for stereoselective synthesis of (E)- and (Z)-β-cyano enones

2021 ◽  
Author(s):  
Ting Liu ◽  
Jie-Ping Wan ◽  
Yunyun Liu
Keyword(s):  
Stereoselective Synthesis ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Practical Method ◽  
Efficient Synthesis ◽  
Metal Free

A highly practical method for C-CN bond formation by C-N bond cleavage on enaminones leading to the efficient synthesis of β-cyano enones is developed. The reactions take place efficiently to...

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