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

Akiyama, Takahiko, Morita, Hisashi, Bachu, Prabhakar, Mori, Keiji, Yamanaka, Masahiro and Hirata, Takashi (2009) Chiral Brønsted acid-catalyzed hydrophosphonylation of imines—DFT study on the effect of substituents of phosphoric acid. Tetrahedron, 65 26: 4950-4956. doi:10.1016/j.tet.2009.03.023


Author Akiyama, Takahiko
Morita, Hisashi
Bachu, Prabhakar
Mori, Keiji
Yamanaka, Masahiro
Hirata, Takashi
Title Chiral Brønsted acid-catalyzed hydrophosphonylation of imines—DFT study on the effect of substituents of phosphoric acid
Journal name Tetrahedron   Check publisher's open access policy
ISSN 0040-4020
1464-5416
Publication date 2009-06-27
Sub-type Article (original research)
DOI 10.1016/j.tet.2009.03.023
Open Access Status Not yet assessed
Volume 65
Issue 26
Start page 4950
End page 4956
Total pages 7
Editor Stephen F. Martin
Place of publication Kidlington, Oxford, United Kingdom
Publisher Pergamon
Language eng
Abstract 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.
Keyword Chiral Brønsted acid
Phosphoric acid
Hydrophosphonylation
α-Amino phosphonate
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ
Additional Notes Special issue: Tetrahedron Young Investigator Award 2009 Recent Advances in Catalysis and Green Chemistry Michael J. Krische

Document type: Journal Article
Sub-type: Article (original research)
Collection: Institute for Molecular Bioscience - Publications
 
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Created: Wed, 21 Mar 2012, 01:09:45 EST by Susan Allen on behalf of Institute for Molecular Bioscience