Enantioselective synthesis of cyclic quaternary α-amino acid derivatives by chiral phosphoric acid catalysis

2017 ◽  
Vol 15 (28) ◽  
pp. 6033-6041 ◽  
Author(s):  
Lei Wang ◽  
Abdul Rahman ◽  
Xufeng Lin
Keyword(s):  
Amino Acid ◽  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Chiral Phosphoric Acid ◽  
Efficient Route ◽  
Quaternary Stereocenter ◽  
High Yields ◽  
Phosphoric Acids

Development of highly enantioselective aza-Friedel–Crafts reaction of N-sulfonyl cyclic ketimines with indoles catalyzed by chiral phosphoric acids, providing an efficient route to indole-containing chiral cyclic α-amino acid derivatives bearing quaternary stereocenter in high yields and up to 98% enantioselectivity.

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

Catalytic Asymmetric Substitution Reaction of 3-Substituted 2-Indolylmethanols with 2-Naphthols

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3684-3692
Author(s):  
Feng Gao ◽  
Yu-Chen Zhang ◽  
Feng Shi ◽  
Jin-Ping Lan ◽  
Yi-Nan Lu ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Substitution Reaction ◽  
Enantioselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Catalytic Asymmetric ◽  
High Yields

A catalytic asymmetric substitution of 3-substituted 2-indolylmethanols with 2-naphthols has been established under the catalysis of chiral phosphoric acid. By this approach, a series of structurally diversified triarylmethane derivatives were obtained in moderate to high yields with good enantioselectivities (up to 97% yield, 95:5 er). This approach not only enriches the chemistry of 2-indolylmethanol-inolved catalytic asymmetric substitutions, but also provides a useful method for the enantioselective synthesis of chiral triarylmethane derivatives.

Highly Enantioselective Biginelli Reaction of Aliphatic Aldehydes Catalyzed by Chiral Phosphoric Acids

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2041-2045 ◽  
Author(s):  
Yongbiao Guo ◽  
Chuanpin Zou ◽  
Zhenhua Gao ◽  
Xiangyan Meng ◽  
Guilan Huang ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Biginelli Reaction ◽  
Aliphatic Aldehyde ◽  
Reaction Conditions ◽  
Aliphatic Aldehydes ◽  
Keto Ester ◽  
Chiral Phosphoric Acid ◽  
Three Component Reaction ◽  
High Yields ◽  
Phosphoric Acids

Several chiral phosphoric acids were evaluated as organocatalysts for the enantioselective Biginelli reaction of aliphatic aldehydes. With a chiral phosphoric acid derived from 3,3′-bis(3,5-di-tert-butyl-4-methoxyphenyl)-1,1′-binaphthalene-2,2′-diol, and after extensive optimization of the reaction conditions, the corresponding dihydropyrimidines were obtained in moderate to high yields with 73–87% ee by a three-component reaction of an aliphatic aldehyde, urea, and a β-keto ester.

Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

2017 ◽  
Vol 4 (7) ◽  
pp. 1407-1410 ◽  
Author(s):  
En Xie ◽  
Abdul Rahman ◽  
Xufeng Lin
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Acid Catalysis ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Quaternary Stereocenter

An enantioselective aza-Friedel–Crafts reaction of indoles with 1-trifluoromethyl-3,4-dihydro-β-carbolines has been developed to afford tetrahydro-β-carbolines with a CF3- and indole-containing quaternary stereocenter by using chiral phosphoric acid catalysis.

Secondary stereocontrolling interactions in chiral Brønsted acid catalysis: study of a Petasis–Ferrier-type rearrangement catalyzed by chiral phosphoric acids

2014 ◽  
Vol 5 (9) ◽  
pp. 3515-3523 ◽  
Author(s):  
Kyohei Kanomata ◽  
Yasunori Toda ◽  
Yukihiro Shibata ◽  
Masahiro Yamanaka ◽  
Seiji Tsuzuki ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Phosphoric Acid ◽  
Acid Catalysis ◽  
Computational Studies ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Chiral Phosphoric Acid ◽  
Acid Catalyzed ◽  
Chiral Bronsted Acid ◽  
Phosphoric Acids

Guided by computational studies, the involvement of non-classical C–H⋯O hydrogen bonds and π–π stacking interactions were found to be crucial for high stereocontrol in a chiral phosphoric acid-catalyzed reaction.

Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid

Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1541-1545 ◽  
Author(s):  
Yuan Jin ◽  
Yasuhiro Honma ◽  
Hisashi Morita ◽  
Masamichi Miyagawa ◽  
Takahiko Akiyama
Keyword(s):  
Phosphoric Acid ◽  
Asymmetric Synthesis ◽  
Vinyl Ether ◽  
31P Nmr ◽  
Cycloaddition Reaction ◽  
Enantioselective Synthesis ◽  
Dipolar Cycloaddition ◽  
New Approach ◽  
Chiral Phosphoric Acid ◽  
High Yields

A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.

Chiral phosphoric acid catalysis: from numbers to insights

2018 ◽  
Vol 47 (4) ◽  
pp. 1142-1158 ◽  
Author(s):  
Rajat Maji ◽  
Sharath Chandra Mallojjala ◽  
Steven E. Wheeler
Keyword(s):  
Phosphoric Acid ◽  
Quantum Chemistry ◽  
Acid Catalysis ◽  
Asymmetric Reactions ◽  
Computational Quantum Chemistry ◽  
Chiral Phosphoric Acid ◽  
Computational Quantum ◽  
Phosphoric Acids

Chiral phosphoric acids (CPAs) have emerged as powerful organocatalysts for asymmetric reactions, and applications of computational quantum chemistry have revealed important insights into the activity and selectivity of these catalysts.

Catalytic, Enantioselective α-Alkylation of Azlactones with Non-Conjugated Alkenes via Directed Nucleopalladation

2018 ◽  
Author(s):  
Sri Nimmagadda ◽  
Mingyu Liu ◽  
Malkanthi Karunananda ◽  
De-Wei Gao ◽  
Omar Apolinar ◽  
...  
Keyword(s):  
Amino Acid ◽  
Phosphoric Acid ◽  
Catalytic Cycle ◽  
Amino Acid Derivatives ◽  
Optimal Conditions ◽  
Wide Range ◽  
Directing Group ◽  
High Yields

A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with non-conjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction and a cleavable bidentate directing group appended to the alkene to control regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal conditions to afford products bearing α,α-disubstituted α-amino acid derivatives with high yields and high enantioselectivity.

Catalytic, Enantioselective α-Alkylation of Azlactones with Non-Conjugated Alkenes via Directed Nucleopalladation

2018 ◽  
Author(s):  
Sri Nimmagadda ◽  
Mingyu Liu ◽  
Malkanthi Karunananda ◽  
De-Wei Gao ◽  
Omar Apolinar ◽  
...  
Keyword(s):  
Amino Acid ◽  
Phosphoric Acid ◽  
Catalytic Cycle ◽  
Amino Acid Derivatives ◽  
Optimal Conditions ◽  
Wide Range ◽  
Directing Group ◽  
High Yields

A palladium(II)-catalyzed enantioselective α-alkylation of azlactones with non-conjugated alkenes is described. The reaction employs a chiral BINOL-derived phosphoric acid as the source of stereoinduction and a cleavable bidentate directing group appended to the alkene to control regioselectivity and stabilize the nucleopalladated alkylpalladium(II) intermediate in the catalytic cycle. A wide range of azlactones were found to be compatible under the optimal conditions to afford products bearing α,α-disubstituted α-amino acid derivatives with high yields and high enantioselectivity.

scholarly journals Enantioselective Synthesis of anti-β-Hydroxy-α-amino Esters via an Organocatalyzed Decarboxylative Aldol Reaction

Synlett ◽  
2017 ◽  
Vol 28 (11) ◽  
pp. 1295-1299 ◽  
Author(s):  
Yoshiji Takemoto ◽  
Taryn March ◽  
Akihiro Murata ◽  
Yusuke Kobayashi
Keyword(s):  
Amino Acid ◽  
Malonic Acid ◽  
Aldol Reaction ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Amino Esters ◽  
Combined Use ◽  
Aldol Addition ◽  
High Yields ◽  
Pentafluorobenzoic Acid

The first enantioselective decarboxylative aldol addition with α-amido-substituted malonic acid half oxyesters (MAHOs) is described. The combined use of a newly designed bifunctional sulfonamide catalyst with pentafluorobenzoic acid as an additive afforded the β-hydroxy-α-amino acid derivatives in moderate to high yields and with high enantioselectivities.

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