A Highly Stereoselective Synthesis of β-Glucosides from Pentaacylglucopyranose and Alkyl Silyl Ether by the Use of a Catalytic Amount of Active Species Generated from Methyltrichlorosilane and Silver Perchlorate

1992 ◽  
Vol 21 (11) ◽  
pp. 2105-2108 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Manabu Katsurada ◽  
Yousuke Iida
Keyword(s):  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Active Species ◽  
Silyl Ether ◽  
Silver Perchlorate

Me3SiCl/HMPA accelerated conjugate addition of catalytic copper reagent. Stereoselective synthesis of enol silyl ether of aldehyde

1986 ◽  
Vol 27 (34) ◽  
pp. 4025-4028 ◽  
Author(s):  
Yoshiaki Horiguchi ◽  
Satoshi Matsuzawa ◽  
Eiichi Nakamura ◽  
Isao Kuwajima
Keyword(s):  
Stereoselective Synthesis ◽  
Conjugate Addition ◽  
Silyl Ether

A Highly Stereoselective Synthesis of α-Glucosides from 1-O-Acetyl Glucose by Use of Tin(IV) Chloride–Silver Perchlorate Catalyst System

1991 ◽  
Vol 20 (4) ◽  
pp. 533-536 ◽  
Author(s):  
Teruaki Mukaiyama ◽  
Tohru Takashima ◽  
Manabu Katsurada ◽  
Hiroyuki Aizawa
Keyword(s):  
Stereoselective Synthesis ◽  
Catalyst System ◽  
Silver Perchlorate

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

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