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

被引：30

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

共 50 条

[31] Natural phosphate and potassium fluoride doped natural phosphate catalysed simple one-pot synthesis of α-amino phosphonates under solvent-free conditions at room temperature
Zahouily, Mohamed
Elmakssoudi, Abdelhakim
Mezdar, Abdessamad
Rayadh, Ahmed
Sebti, Said
CATALYSIS COMMUNICATIONS, 2007, 8 (03) : 225 - 230
[32] An efficient one-pot synthesis of dihydropyrano[c]chromenes and amino-2-chromenes under solvent-free conditions
Habibi, Davood
Shamsian, Atefeh
JOURNAL OF CHEMICAL RESEARCH, 2013, (04) : 253 - 255
[33] One-Pot Synthesis of Imidazole Derivatives Under Solvent-Free Condition
Zhang, Qiu-Gen
Xie, Yu
Hu, Jin-Gang
Liu, Jin-Mei
Wang, Juan
Zhong, Rong
Gao, Yun-Hua
ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (10) : 4611 - 4613
[34] Highly Efficient Catalyst-Free One-Pot Synthesis of Dithiocarbamates under Solvent-Free Conditions
Guo, Shengrong
Yuan, Yanqin
Zhang, Chunniu
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (05) : 907 - 914
[35] A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation
Balalaie, S
Hashemi, MM
Akhbari, M
TETRAHEDRON LETTERS, 2003, 44 (08) : 1709 - 1711
[36] A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions
Maleki, Behrooz
Barzegar, Shahram
Sepehr, Zeinalabedin
Kermanian, Mina
Tayebee, Reza
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (05) : 757 - 765
[37] Convenient, multicomponent, one-pot synthesis of highly substituted pyridines under solvent-free conditions
Mobinikhaledi, Akbar
Asadbegi, Sajad
Bodaghifard, Mohammad Ali
SYNTHETIC COMMUNICATIONS, 2016, 46 (19) : 1605 - 1611
[38] A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions
Behrooz Maleki
Shahram Barzegar
Zeinalabedin Sepehr
Mina Kermanian
Reza Tayebee
Journal of the Iranian Chemical Society, 2012, 9 : 757 - 765
[39] Synthesis of β-enaminones by ionic liquid catalysis:: A one-pot condensation under solvent-free conditions
Martins, Marcos A. P.
Frizzo, Clarissa P.
Moreira, Dayse N.
Rosa, Fernanda A.
Marzari, Mara R. B.
Zanatta, Nilo
Bonacorso, Helio G.
CATALYSIS COMMUNICATIONS, 2008, 9 (06) : 1375 - 1378
[40] One-Pot Synthesis of Pyrimido[1,2-a]benzimidazoles under Solvent-Free Conditions
Ghorbani-Vaghei, Ramin
Toghraei-Semiromi, Zahra
Karimi-Nami, Rahman
Salimi, Zahra
HELVETICA CHIMICA ACTA, 2014, 97 (07) : 979 - 984

← 1 2 3 4 5 →