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
[41]   Synthesis and crystal structure of ((6R,7S)-3-ethyl-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanone hemihydrate, 2(C19H18N4OS) • H2O [J].
Ding, Qichun ;
Yang, Ruya ;
Yao, Peipao .
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2020, 235 (05) :1157-1159
[42]   STEREOSELECTIVE REACTION OF (+/-)-7-PHENYLDINAPHTHO[2,1-B-1',2'-D]PHOSPHOLE WITH AN OPTICALLY-ACTIVE PALLADIUM COMPLEX - MOLECULAR-STRUCTURE AND FLUXIONAL BEHAVIOR OF PD((S)-C6H4CH(CH3)N(CH3)2)((P)-PPH(C20H12))CL [J].
TANI, K ;
TASHIRO, H ;
YOSHIDA, M ;
YAMAGATA, T .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 469 (02) :229-236
[43]   Investigations on 2,3′-biquinolines 22. Novel and convenient method for the synthesis of benzo[5,6]indolizino-[2,1-b]quinolinium-13-thiolates and benzo-[5,6]indolizino[1,2-c]quinoline-6(5H)-thiones [J].
Moiseev D.V. ;
Goncharov V.I. ;
Aksenov A.V. .
Chemistry of Heterocyclic Compounds, 2007, 43 (06) :715-717
[44]   Controlled synthesis of mono-substituted diphosphine iron thiocarboxylate complexes CpFe(CO)(Ph2P(CH2)nPPh2)SCOR [n=1 (dppm), n=2 (dppe)].: X-ray crystal structure of CpFe(CO)(dppm-S)SCO-3,5-(NO2)2C6H3 [J].
El-khateeb, M ;
Jibril, I ;
Barakat, H ;
Rheinwald, G ;
Lang, HR .
POLYHEDRON, 2003, 22 (27) :3445-3449
12345