scholarly journals PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

2021 ◽  
pp. 174751982098753
Author(s):  
Xiaofang Wu ◽  
Lei Zhou ◽  
Fangshao Li ◽  
Jing Xiao
Keyword(s):  
Acid Chloride ◽  
Bioactive Molecules ◽  
Mechanistic Studies ◽  
One Pot ◽  
Tert Butyl ◽  
Butyl Esters

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

scholarly journals 3-(tert-Butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine

Molbank ◽  
10.3390/m1196 ◽  
2021 ◽  
Vol 2021 (1) ◽  
pp. M1196
Author(s):  
Diana Becerra ◽  
Hugo Rojas ◽  
Juan-Carlos Castillo
Keyword(s):  
Reductive Amination ◽  
2D Nmr ◽  
Reduction Reaction ◽  
Reaction Sequence ◽  
One Pot ◽  
Isolation And Purification ◽  
Tert Butyl ◽  
The One ◽  
Synthetic Intermediate

We reported an efficient one-pot two-step synthesis of 3-(tert-butyl)-N-(4-methoxybenzyl)-1-methyl-1H-pyrazol-5-amine 3 in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(tert-butyl)-1-methyl-1H-pyrazol-5-amine 1 and p-methoxybenzaldehyde 2. The one-pot reductive amination proceeded by the formation in situ of the N-(5-pyrazolyl)imine 4 as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized N-heterocyclic amine 3 was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis.

An efficient method for the preparation of tert-butyl esters from benzyl cyanide and tert-butyl hydroperoxide under the metal free condition

RSC Advances ◽  
2016 ◽  
Vol 6 (104) ◽  
pp. 102023-102027 ◽  
Author(s):  
Xiuling Chen ◽  
Yan Li ◽  
Minghu Wu ◽  
Haibing Guo ◽  
Longqiang Jiang ◽  
...  
Keyword(s):  
Efficient Method ◽  
Bond Cleavage ◽  
Bond Formation ◽  
One Pot ◽  
Free Condition ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Butyl Esters ◽  
Tert Butyl Hydroperoxide

A novel protocol to synthesize tert-butyl esters from benzyl cyanides and tert-butyl hydroperoxide has been successfully achieved. Csp3–H bond oxidation, C–CN bond cleavage and C–O bond formation proceeded smoothly in one pot under the metal-free condition.

Organocatalytic Domino Annulation of In Situ Generated tert-Butyl 2-Hydroxybenzylidenecarbamates with 2-Isothiocyanato-1-indanones for Synthesis of Bridged and Fused Ring Heterocycles

2021 ◽  
Author(s):  
Xiqiang Hou ◽  
Ye Lin ◽  
Da-Ming Du
Keyword(s):  
One Pot ◽  
Tert Butyl ◽  
Fused Ring

A one-pot efficient asymmetric domino annulation of 2-isothiocyanato-1-indanones with tert-butyl 2-hydroxybenzylidenecarbamates in situ generated from 2-hydroxyaryl-substituted α-amido sulfones was developed. This reaction firstly provided a powerful tool for the enantioselective...

Enantioselective Synthesis of 2-Substituted Pyrrolidines via Intramolecular­ Reductive Amination

Synthesis ◽  
2019 ◽  
Vol 51 (13) ◽  
pp. 2713-2719
Author(s):  
Huan Zhou ◽  
Wenlei Zhao ◽  
Tao Zhang ◽  
Haodong Guo ◽  
Haizhou Huang ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Enantioselective Synthesis ◽  
One Pot ◽  
Tert Butyl

Catalyzed by the complex generated in situ from iridium and the chiral ferrocene ligand, tert-butyl (4-oxo-4-arylbutyl)carbamate substrates were deprotected and then reductively cyclised to form 2-substituted arylpyrrolidines in a one-pot manner, in which the intramolecular reductive amination was the key step. A range of chiral 2-substituted arylpyrrolidines were synthesised in up to 98% yield and 92% ee.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

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