An Alternative Route for Synthesis of Chiral 4-Substituted 1-Arenesulfonyl-2-imidazolidinones: Unusual Utility of (4S, 5S)- and (4R, 5R)-4,5-Dimethoxy-2-imidazolidinones and X-Ray Crystallography

被引：2

作者：

Al-Swaidan, Ibrahim A. ^{[1
]}

Alanazi, Amer M. ^{[1
]}

El-Azab, Adel S. ^{[1
,2
]}

Abdel-Aziz, Alaa A. -M. ^{[1
,3
]}

机构：

[1] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia

[2] Al Azhar Univ, Fac Pharm, Dept Organ Chem, Cairo 11884, Egypt

[3] Univ Mansoura, Fac Pharm, Dept Med Chem, Mansoura 35516, Egypt

来源：

JOURNAL OF CHEMISTRY | 2013年 / 2013卷

关键词：

REAGENTS;

D O I：

10.1155/2013/349519

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unusual synthesis of (S)-1-arenesulfonyl-4-(1-adamantyl)-2-imidazolidinones 15a-d and (R)-1-arenesulfonyl-4-tert-butyl-2- imidazolidinones 19a-d has been developed from trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 as chiral synthons. Diastereomerically pure trans-1-apocamphanecarbonyl-4,5-dimethoxy-2-imidazolidinones 6 and 7 were successfully subjected to regioselective reduction using bulky organocuprates that afforded 1-apocamphanecarbonyl-5-methoxy-2-imidazolidinones 10 and 11. This new finding was used for synthesis of chiral 4-substituted 2-imidazolidinones 15a-d and 19a-d through the corresponding intermediates 13 and 17 by treatment with steric bulky tert-butylcuprate or 1-adamantylcuprate.

引用

页数：5

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