Asymmetric Allylic Amination of Morita–Baylis–Hillman Adducts with Simple Aromatic Amines by Nucleophilic Amine Catalysis

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 703-708 ◽  
Author(s):  
Xin Chen ◽  
Shuai Zhao ◽  
Zhi-Li Chen ◽  
Xue Rui ◽  
Ming-Mei Gao
Keyword(s):  
Catalytic System ◽  
Aromatic Amines ◽  
Cyclic Imide ◽  
Allylic Amination ◽  
System A ◽  
Amination Reaction ◽  
Amine Catalysis ◽  
High Yields ◽  
Inorganic Fluorides ◽  
Amination Product

Asymmetric allylic amination of Morita–Baylis–Hillman (MBH) adducts with simple aromatic amines is successfully realized by nucleophilic amine catalysis. A range of substituted α-methylene-β-arylamino esters is accessed in moderate to high yields (up to 88%) and with excellent enantioselectivities (up to 97% ee). Inorganic fluorides are found to be able to improve the enantioselectivity of the allylic amination reaction. A pyrrole-2-carboxylate and a cyclic imide are also compatible with this catalytic system. A chiral 2,3-dihydroquinolin-4-one derivative is easily obtained from the allylic amination product.

Efficient Copper-Catalysed Synthesis of Carbazoles by Double N-Arylation of Primary Amines with 2,2′-Dibromobiphenyl in the Presence of Air

Synlett ◽  
2021 ◽  
Author(s):  
Tran Quang Hung ◽  
Tuan Thanh Dang ◽  
Peter Langer ◽  
Ha Nam Do ◽  
Nguyen Minh Quan ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Aliphatic Amines ◽  
Primary Amines ◽  
Coupling Reactions ◽  
Carbazole Derivatives ◽  
High Yields

AbstractAn efficient Cu-catalyzed synthesis of carbazole derivatives is reported, which proceeds by double C–N coupling reactions of 2,2′-dibromobiphenyl and amines in the presence of air. The reaction is robust, proceeds in high yields, and tolerates a series of amines including neutral, electron-rich, electron-deficient aromatic amines and aliphatic amines.

Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane

2021 ◽  
Author(s):  
Xin Li ◽  
Guoliang Gao ◽  
Songtao He ◽  
Qiuling Song
Keyword(s):  
Catalytic System ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
High Yields

Presented herein is the first 1,6-conjugate addition of diborylmethane, which is promoted by a simple and inexpensive copper catalytic system. This method features high yields, good selectivities and broad functional...

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

scholarly journals Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives

ChemistryOpen ◽  
2015 ◽  
Vol 5 (1) ◽  
pp. 65-70 ◽  
Author(s):  
Mariya A. Timoshenko ◽  
Yurii V. Kharitonov ◽  
Makhmut M. Shakirov ◽  
Irina Yu. Bagryanskaya ◽  
Elvira E. Shults
Keyword(s):  
Allylic Amination ◽  
Isopimaric Acid ◽  
Amination Reaction ◽  
Synthetic Studies

A Brønsted acid-promoted asymmetric intramolecular allylic amination of alcohols

2018 ◽  
Vol 16 (3) ◽  
pp. 380-383 ◽  
Author(s):  
Jianqiao Zhou ◽  
Hexin Xie
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Allylic Amination ◽  
Amination Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

An asymmetric intramolecular allylic amination reaction catalyzed by a chiral Brønsted acid is disclosed, affording biologically intriguing chiral 2-substituted hydroquinolines in up to 90% yield and with up to 93% ee.

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.

scholarly journals Regioselective Copper-Catalysed Amination of Halobenzoic Acids using Aromatic Amines

2007 ◽  
Vol 2007 (10) ◽  
pp. 587-589 ◽  
Author(s):  
Mohan Babu Maradolla ◽  
Amaravathi Mandha ◽  
Chandra Mouli Garimella
Keyword(s):  
Microwave Irradiation ◽  
Aromatic Amines ◽  
Reaction Times ◽  
Efficient Catalyst ◽  
High Yields

Copper dipyridine dichloride (CuPy2Cl2) has been found to be an efficient catalyst for the synthesis of N-arylanthranilic acids from ortho halobenzoic acids and aromatic amines under microwave irradiation. Some of the advantages of this method are high chemoselectivity, ease of operation, less reaction times and high yields. (61–98%).

Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated N-acylpyrazoles

2016 ◽  
Vol 52 (78) ◽  
pp. 11677-11680 ◽  
Author(s):  
Pan Li ◽  
Xinquan Hu ◽  
Xiu-Qin Dong ◽  
Xumu Zhang
Keyword(s):  
Catalytic System ◽  
Asymmetric Hydrogenation ◽  
Enantioselective Hydrogenation ◽  
High Yields

We successfully extended our Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system to asymmetric hydrogenation of α,β-unsaturated N-acylpyrazoles affording products with high yields and excellent enantioselectivities (up to 97% yield, 99% ee).

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