Diastereo- and Enantioselective Synthesis of Highly Functionalized Tetrahydropyridines by Recyclable Novel Bifunctional C2-Symmetric Ionic Liquid-Supported (S)-Proline Organocatalyst

被引：4

作者：

Davanagere, Prabhakara Madivalappa ^{[1
]}

De, Mrinmoy ^{[2
]}

Chanda, Kaushik ^{[1
]}

Maiti, Barnali ^{[1
]}

机构：

[1] Vellore Inst Technol, Sch Adv Sci, Dept Chem, Vellore 632014, India

[2] Indian Inst Sci, Dept Organ Chem, Bengaluru 560012, India

来源：

CATALYSTS | 2023年 / 13卷 / 01期

关键词：

asymmetric catalysis; multicomponent reactions; stereoselectivities; functionalized tetrahydropyridines; ONE-POT SYNTHESIS; MORITA-BAYLIS-HILLMAN; MULTICOMPONENT REACTIONS; EFFICIENT; 5-COMPONENT; PROLINE; FACILE; ATOM; SOLVENTS; CATALYST;

D O I：

10.3390/catal13010209

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient, novel bifunctional C-2-symmetric ionic liquid-supported (S)-proline organocatalyst 7 was developed for a one-pot, five-component reaction involving beta-keto esters 8, aryl aldehydes 9, and aryl amines 10, affording highly functionalized tetrahydropyridines 11a-o by simultaneous generation of fives bonds and two stereogenic centers with extraordinary diastereo- and enantioselectivities (up to >99:1 dr, 95:5 er) in isopropanol with high yields (up to 92%). This protocol provides quick access to diverse enantio-enriched, highly functionalized diastereo- and enantioselective tetrahydropyridines in a green medium without any column chromatographic purification. The catalyst was recycled five times without significant loss of its catalytic activity.

引用

页数：16

共 5 条

[1] Bifunctional C2-symmetric ionic liquid-supported (S)-proline as a recyclable organocatalyst for Mannich reactions in neat condition
Davanagere, Prabhakara Madivalappa
Maiti, Barnali
RESULTS IN CHEMISTRY, 2021, 3
[2] Ionic Liquid-Supported (ILS) (S)-Pyrrolidine Sulfonamide, a Recyclable Organocatalyst for the Highly Enantioselective Michael Addition to Nitroolefins
Ni, Bukuo
Zhang, Qianying
Dhungana, Kritanjali
Headley, Allan D.
ORGANIC LETTERS, 2009, 11 (04) : 1037 - 1040
[3] C2-Symmetric Recyclable Organocatalyst for Enantioselective Strecker Reaction for the Synthesis of α-Amino Acid and Chiral Diamine- an Intermediate for APN Inhibitor
Saravanan, S.
Sadhukhan, Arghya
Khan, Noor-ul H.
Kureshy, Rukhsana I.
Abdi, Sayed H. R.
Bajaj, Hari C.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (09): : 4375 - 4384
[4] Highly regio-, diastereo-, and enantioselective C-H insertions of methyl aryldiazoacetates into cyclic N-BOC-protected amines.: Asymmetric synthesis of novel C2-symmetric amines and threo-methylphenidate
Davies, HML
Hansen, T
Hopper, DW
Panaro, SA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) : 6509 - 6510
[5] Highly regio-, diastereo-, and enantioselective C-H insertions of methyl aryldiazoacetates into cyclic N-boc-protected amines. Asymmetric synthesis of novel C2-symmetric amines and threo-methylphenidate
Davies, Huw M.L.
Hansen, Tore
Hopper, Darrin W.
Panaro, Stephen A.
Journal of the American Chemical Society, 121 (27):

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