Chiral Brønsted acid-catalyzed hydrophosphonylation of imines—DFT study on the effect of substituents of phosphoric acid

The enantioselective hydrophosphonylation reaction of diisopropyl phosphite with aldimine furnished α-amino phosphonates with high enantioselectivities by means of a chiral phosphoric acid. DFT calculation of the effect of 3,3′-substituents of the phosphoric acid revealed the reason for the high ena...

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Bibliographic Details
Published in:Tetrahedron 2009-06, Vol.65 (26), p.4950-4956
Main Authors: Akiyama, Takahiko, Morita, Hisashi, Bachu, Prabhakar, Mori, Keiji, Yamanaka, Masahiro, Hirata, Takashi
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Chiral Brønsted acid
DFT calculation
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Hydrophosphonylation
Miscellaneous
Organic chemistry
Phosphoric acid
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
α-Amino phosphonate
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Summary:The enantioselective hydrophosphonylation reaction of diisopropyl phosphite with aldimine furnished α-amino phosphonates with high enantioselectivities by means of a chiral phosphoric acid. DFT calculation of the effect of 3,3′-substituents of the phosphoric acid revealed the reason for the high enantioselectivities. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.03.023