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

被引：73

作者：

Akiyama, Takahiko ^{[1
]}

Morita, Hisashi ^{[1
]}

Bachu, Prabhakar ^{[1
]}

Mori, Keiji ^{[1
]}

Yamanaka, Masahiro ^{[2
]}

Hirata, Takashi ^{[2
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

[2] Rikkyo Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718501, Japan

来源：

TETRAHEDRON | 2009年 / 65卷 / 26期

关键词：

Chiral Bronsted acid; Phosphoric acid; Hydrophosphonylation; alpha-Amino phosphonate; DFT calculation; MANNICH-TYPE REACTION; ALPHA-AMINO PHOSPHONATES; FRIEDEL-CRAFTS REACTION; DIELS-ALDER REACTION; HETEROBIMETALLIC LANTHANOID COMPLEXES; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; ASYMMETRIC-SYNTHESIS; TRANSFER HYDROGENATION; ALKYLATION; ALDEHYDES;

D O I：

10.1016/j.tet.2009.03.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective hydrophosphonylation reaction of diisopropyl phosphite with aldimine furnished alpha-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. (C) 2009 Elsevier Ltd. All rights reserved,

引用

页码：4950 / 4956

页数：7

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