Uncatalyzed One-Pot Diastereoselective Synthesis of α-Amino Phosphonates Under Solvent-Free Conditions

被引：29

作者：

Tibhe, Gaurao D. ^{[1
]}

Lagunas-Rivera, Selene ^{[1
]}

Vargas-Diaz, Elena ^{[2
]}

Garcia-Barradas, Oscar ^{[3
]}

Ordonez, Mario ^{[1
]}

机构：

[1] Univ Autonoma Estado Morelos, Ctr Invest Quim, Cuernavaca 61209, Morelos, Mexico

[2] IPN, Escuela Nacl Ciencias Biol, Mexico City 11340, DF, Mexico

[3] Univ Veracruzana, Unidad Serv Apoyo Resoluc Analit, Xalapa 91190, Veracruz, Mexico

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 34期

关键词：

Diastereoselectivity; alpha-Amino phosphonates; Kabachnik-Fields reaction; alpha-Amino phosphonic acids; Phosphorus; Multicomponent reactions; KABACHNIK-FIELDS REACTION; STATE ANALOG INHIBITORS; ASYMMETRIC-SYNTHESIS; ACID-DERIVATIVES; ENANTIOSELECTIVE HYDROPHOSPHONYLATION; STEREOSELECTIVE-SYNTHESIS; AMINOPHOSPHONIC ACIDS; BIOLOGICAL-ACTIVITY; HIV-PROTEASE; PHOSPHONOPEPTIDES;

D O I：

10.1002/ejoc.201001096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Uncatalyzed one-pot, three-component reactions of aldehydes, chiral alpha-methylamines, and dimethyl phosphite under solvent-free conditions were used for the diastereoselective synthesis of alpha-amino phosphonates. The reactions proceeded with extremely high efficiency under mild conditions and gave good yields and diastereoselectivities (70:30 to 93:7 dr). This approach could be useful for the large-scale synthesis of several alpha-amino phosphonates.

引用

页码：6573 / 6581

页数：9

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