DIASTEREOSELECTIVE LITHIATION OF N-SILYL-PROTECTED (S)-TETRAHYDRO-1H-PYRROLO[1,2-c]IMIDAZOL-3(2H)-ONE

被引：3

作者：

Metallinos, Costa ^{[1
]}

Sadraei, Seyed Iraj ^{[1
]}

Zhukovskaya, Nadezda ^{[1
]}

机构：

[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

来源：

HETEROCYCLES | 2014年 / 88卷 / 01期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Proline Hydantoin; Diastereoselective Reaction; Lithiation; Triethylsilyl Protecting Group; Pyrroloimidazolinone; CATALYZED ALPHA-ARYLATION; DYNAMIC THERMODYNAMIC RESOLUTION; ASYMMETRIC DEPROTONATION; BOC-PYRROLIDINE; ENANTIOSELECTIVE SYNTHESES; PRODUCT STEREOSPECIFICITY; ENANTIOMERIZATION; STEREOSELECTIVITY; SUBSTITUTION; CYCLIZATION;

D O I：

10.3987/COM-13-S(S)29

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An L-proline-derived imidazolone protected with an N-triethylsilyl (N-TES) group undergoes diastereoselective lithiation-electrophile quench to give C5-substituted products with syn stereochemistry. Unlike the previous N-t-Bu analogues, the N-TES derivatives may be easily N-desilylated to give secondary ureas that serve as precursors to N-phenyl chiral bicyclic guanidines.

引用

收藏

页码：347 / 362

页数：16

相关论文

共 44 条

[21] Enantiomerization of chiral 2,3,3a,4-tetrahydro-1H-pyrrolo[2,1-c][1,2,4] benzothiadiazine 5,5-dioxide by stopped-flow multidimensional HPLC [J].

Cannazza, Giuseppe ;

Carrozzo, Marina M. ;

Braghiroli, Daniela ;

Parenti, Carlo .

JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2008, 875 (01) :192-199

[22] Palladium-Catalyzed Dual C(sp2)-H Functionalization of Indole-2-carboxamides Involving a 1,2-Acyl Migration: A Synthesis of Indolo[3,2-c]quinolinones [J].

Kong, Lingkai ;

Zheng, Zhong ;

Tang, Rong ;

Wang, Mengdan ;

Sun, Yue ;

Li, Yanzhong .

ORGANIC LETTERS, 2018, 20 (18) :5696-5699

[23] I2-catalyzed one-pot synthesis of pyrrolo[1,2-a]-quinoxaline and imidazo[1,5-a]quinoxaline derivatives via sp3 and sp2 C-H cross-dehydrogenative coupling [J].

Zhang, Zeyuan ;

Xie, Caixia ;

Tan, Xiaochen ;

Song, Gaolei ;

Wen, Leilin ;

Gao, He ;

Ma, Chen .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (08) :942-946

[24] Base-Mediated Regioselective Synthesis of Pyrrolo[3,4-b]quinolin-1-one and Benzo[b][1,6]Naphthyridin-1(2H)-One Derivatives from o-Alkynyl Quinoline-3-carbonitriles and Their Photophysical Properties [J].

Kumar, Vipin ;

Sharma, Shubham ;

Pandey, Satyendra Kumar ;

Singh, Virender .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (37)

[25] Synthesis of Quinolino[3′,4′:4,5] pyrrolo[1,2-f]phenanthridines by Regioselective Sonogashira Reaction Followed by Domino C-N Coupling/Hydroamination/C-H Arylation [J].

Ngo Nghia Pham ;

Salman, Ghazwan Ali ;

Ponce, Marian Blanco ;

Tuan Thanh Dang ;

Spannenberg, Anke ;

Ehlers, Peter ;

Langer, Peter .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (26) :3865-3873

[26] Synthesis of the First Representatives of Thieno[3,2-c][1,7]naphthyridine Derivatives Based on 3-Amino-6-methyl-4-(2-thienyl)pyridin-2(1H )-one [J].

Kulakov, Ivan V. ;

Matsukevich, Mariya V. ;

Levin, Maxim L. ;

Palamarchuk, Irina V. ;

Seilkhanov, Tulegen M. ;

Fisyuk, Alexander S. .

SYNLETT, 2018, 29 (13) :1741-1744

[27] Mild Synthesis of 3,4-Dihydroisoquinolin-1(2H)-ones via Rh(III)-Catalyzed Tandem C-H-Allylation/N-Alkylation Annulation with 2-Methylidenetrimethylene Carbonate [J].

Xie, Hui ;

Zeng, Yao-Fu ;

Shu, Bing ;

Liang, Jin-Yi ;

Huang, Zhuo-Jun ;

Chen, Shao-Yong ;

Zheng, Yi-Chuan ;

Liu, Yan-Zhi ;

Zhang, Shang-Shi .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23) :17063-17070

[28] A Versatile Approach for the Synthesis of 8H-Thieno[2,3-b]indoles and N-[2-(2-N-(R1,R2)-2-Thioxoacetyl)-phenyl]acetamides from 1-Acetyl-1,2-dihydro-3H-indol-3-one (Acetylindoxyl) and Its Derivatives: A Novel Synthesis of Intermediate (1-Acetyl-1H-indol-3-yl)malononitrile/cyanoacetates [J].

Velezheva, Valeriya S. ;

Lepyoshkin, Alexander Yu. ;

Turchin, Konstantin F. ;

Fedorova, Irina N. ;

Peregudov, Alexander S. ;

Brennan, Patrick J. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (02) :225-236

[29] Synthesis of chromeno[3,4-c][1,2]oxazine-N-oxides via formal [4+2] cycloaddition of 3-nitro-2-trihalomethy1-2H-chromenes with cyclohexanone and pinacolone enamines [J].

Korotaev, Vladislav Yu ;

Barkov, Alexey Yu ;

Matochkina, Evgeniya G. ;

Kodess, Mikhail I. ;

Sosnovskikh, Vyacheslav Ya .

TETRAHEDRON, 2014, 70 (34) :5161-5167

[30] Crystal structure of 2-(4-nitroanilino)-4,5,6,7-tetrahydro-1,2-benzisothiazolium perchlorate, [C13H14N3O2S][ClO4] [J].

Zakharova, Valeria M. ;

Sieler, Joachim ;

Schulze, Baerbel .

ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2009, 224 (01) :133-134

← 1 2 3 4 5 →