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

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