Cu-Catalyzed electrophilic amination of internal alkynes via hydroalumination

2017 ◽  
Vol 15 (4) ◽  
pp. 790-795 ◽  
Author(s):  
Hongju Yoon ◽  
Yuna Kim ◽  
Yunmi Lee
Keyword(s):  
Efficient Method ◽  
Electrophilic Amination ◽  
Amination Reaction ◽  
Internal Alkynes ◽  
Aryl Acetylenes

A straightforward and efficient method for the synthesis of 1,2-diaryl-substituted enamines through the Cu-catalyzed electrophilic amination reaction of O-benzoyl hydroxylamines with vinylaluminum reagents generated in situ from the Ni-catalyzed hydroalumination of readily accessible internal aryl acetylenes is described.

A facile one pot route for the synthesis of imide tethered peptidomimetics

2016 ◽  
Vol 14 (2) ◽  
pp. 556-563 ◽  
Author(s):  
Veladi Panduranga ◽  
Girish Prabhu ◽  
Roopesh Kumar ◽  
Basavaprabhu Basavaprabhu ◽  
Vommina V. Sureshbabu
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Efficient Method ◽  
One Pot ◽  
Protected Amino Acid

A simple and efficient method for the synthesis of N,N’-orthogonally protected imide tethered peptidomimetics is presented. The imide peptidomimetics were synthesized by coupling the in situ generated selenocarboxylate of Nα-protected amino acids with Nα-protected amino acid azides in good yields.

Synthesis of Symmetrical Dipurine-Nucleoside Diphosphates from the Corresponding Nucleoside Phosphoropiperidates

2014 ◽  
Vol 1023 ◽  
pp. 55-58
Author(s):  
Xiao Chuan Li ◽  
Shan Shan Gong ◽  
Qi Sun
Keyword(s):  
Efficient Method ◽  
Good Yield ◽  
Purine Bases ◽  
Hydrolysis Of

A general and efficient method for the preparation of symmetrical dinucleoside diphosphates with purine bases has been developed. Ap2A and Gp2G were synthesized from the in situ hydrolysis of corresponding nucleoside 5′-phosphoropiperidates with 4,5-dicyanoimidazole as the activator. This method features easily accessible starting materials, simple procedures, and good yield.

The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Brønsted Acids

Synlett ◽  
2018 ◽  
Vol 29 (15) ◽  
pp. 2015-2018 ◽  
Author(s):  
William Wulff ◽  
Xin Zhang ◽  
Yijing Dai
Keyword(s):  
Silica Gel ◽  
Efficient Method ◽  
Bronsted Acids ◽  
High Yields

An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.

scholarly journals Fluorohydration of alkynes via I(I)/I(III) catalysis

2020 ◽  
Vol 16 ◽  
pp. 1627-1635 ◽  
Author(s):  
Jessica Neufeld ◽  
Constantin G Daniliuc ◽  
Ryan Gilmour
Keyword(s):  
Substrate Specificity ◽  
Small Molecule ◽  
Physical Organic ◽  
Internal Alkynes ◽  
Biological Catalysis

Substrate specificity is ubiquitous in biological catalysis, but less pervasive in the realm of small-molecule catalysis. Herein, we disclose an intriguing example of substrate specificity that was observed whilst exploring catalysis-based routes to generate α-fluoroketones from terminal and internal alkynes under the auspices of I(I)/I(III) catalysis. Utilising p-TolI as an inexpensive organocatalyst with Selectfluor® and amine/HF mixtures, the formation of protected α-fluoroketones from simple alkynes was realised. Whilst the transient p-TolIF2 species generated in situ productively engaged with pentynyl benzoate scaffolds to generate the desired α-fluoroketone motif, augmentation or contraction of the linker suppressed catalysis. The prerequisite for this substructure was established by molecular editing and was complemented with a physical organic investigation of possible determinants.

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

2019 ◽  
Vol 55 (64) ◽  
pp. 9547-9550 ◽  
Author(s):  
Yaping Shang ◽  
Krishna Jonnada ◽  
Subhash Laxman Yedage ◽  
Hua Tu ◽  
Xiaofeng Zhang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Nitroso Group ◽  
Group Strategy ◽  
Internal Alkynes ◽  
Directing Group ◽  
Catalyzed Reactions ◽  
Indole Synthesis

Rh-Catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group.

Asymmetric α-Amination Reaction of Alkenoate Cyclic Esters Catalyzed by Chiral Tin Alkoxides

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 738-742
Author(s):  
Akira Yanagisawa ◽  
Yoshiki Yamashita ◽  
Chika Uchiyama ◽  
Ryuta Nakano ◽  
Moe Horiguchi ◽  
...  
Keyword(s):  
Optically Active ◽  
Cyclic Esters ◽  
Amination Reaction ◽  
High Yields ◽  
Sodium Alkoxide

A catalytic enantioselective α-amination reaction of alkenoate cyclic esters with dialkyl azodicarboxylates was achieved by using a 3,3′-di(1-naphthyl)-substituted (R)-BINOL–dibromostannane complex as a chiral precatalyst in the presence of a sodium alkoxide and an alcohol. Optically active α-hydrazino ketones were obtained in moderate to high yields and with up to 91% ee in the presence of the chiral tin alkoxide generated in situ.

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