Proline-β3-Amino-Ester Dipeptides as Efficient Catalysts for Enantioselective Direct Aldol Reaction in Aqueous Medium

被引：20

作者：

De Nisco, Mauro ^{[1
]}

Pedatella, Silvana ^{[1
]}

Ullah, Hidayat ^{[2
]}

Zaidi, Javid H. ^{[2
]}

Naviglio, Daniele ^{[1
]}

Ozdamar, Ozgur ^{[3
]}

Caputo, Romualdo ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

[2] Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan

[3] Ondokuz Mayis Univ, Fen Edebiyat Fak, Kimya Bolumu, TR-55200 Samsun, Turkey

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期

关键词：

BETA-AMINO ACIDS; ORGANOCATALYTIC REACTIONS; PROLINE-DERIVATIVES; WATER; ALPHA; ESTERS;

D O I：

10.1021/jo902106r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dipeptides obtained from L-proline and beta(3)-L-amino acids are reported to catalyze enantioselective direct aldol reaction in aqueous medium, leading to significant anti: syn diastereomeric ratios and enantiomeric excesses. The simple introduction of a polar substituent at the C-2 position of the beta(3)-L-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst.

引用

页码：9562 / 9565

页数：4

共 5 条

[1] Diastereo- and Enantioselective Direct Aldol Reactions in Aqueous Medium: A New Highly Efficient Proline-Sugar Chimeric Catalyst
Pedatella, Silvana
De Nisco, Mauro
Mastroianni, Domenico
Naviglio, Daniele
Nucci, Ada
Caputo, Romualdo
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1443 - 1446
[2] Highly Efficient Small Organic Molecules for Enantioselective Direct Aldol Reaction in Organic and Aqueous Media
Vishnumaya, Monika Raj
Singh, Vinod K.
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) : 4289 - 4297
[3] Isothiouronium salt based chiral proline amide as efficient bifunctional organocatalyst for direct asymmetric aldol reactions in aqueous medium
Yeo, Hyoung Min
Kang, Sungmin
Kim, Taek Hyeon
TETRAHEDRON LETTERS, 2021, 80
[4] New Mesoporous Silica-Supported Organocatalysts Based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, Reusable, and Heterogeneous Catalysts for the Asymmetric Aldol Reaction
Sanchez-Antonio, Omar
Romero-Sedglach, Kevin A.
Vazquez-Orta, Erika C.
Juaristi, Eusebio
MOLECULES, 2020, 25 (19):
[5] An efficient and green reaction of isatins, 3-amino-1-phenyl-2-pyrazolin-5-one (3-amine-1H-pyrazole), and β-diketone in aqueous medium
Wang, Zhansheng
Xu, Hui
Yan, Lirong
Li, Qingyang
Rong, Liangce
MOLECULAR DIVERSITY, 2017, 21 (04) : 985 - 997

← 1 →