Scope and limitations of the nitro-Mannich reaction for the stereoselective synthesis of 1,2-diamines

被引：61

作者：

Anderson, JC ^{[1
]}

Blake, AJ ^{[1
]}

Howell, GP ^{[1
]}

Wilson, C ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 02期

关键词：

D O I：

10.1021/jo048304h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DIAGRAM The acetic acid-promoted addition of lithium nitropropanate and the Lewis acid-catalyzed [Sc-(OTf)(3), Cu(OTf)(2), or Ti(OiPr)(4)] addition of trimethylsilyl nitropropanate to a rang of heteroaromatic and simple aliphatic aldimines gave anti-rich (similar to3-19:1) beta-nitroamines in > 95 % yields as the kinetic products. It was found that a nonpolar N-imine protecting group was essential for reactivity with the o-methoxybenzyl (OMB) group giving better selectivities and yields than p-methoxybenzyl (PMB) or p-methoxyphenyl (PMP) in the Lewis acid-catalyzed addition reactions. Reduction with SmI2, treatment with COCl2, followed by OMB deprotection gave diastereomerically pure cis-imidazolidinones in 55-79 % overall yield from imine. Preliminary results have shown that acetic acid can catalyze the reaction of N-OMB-benzylideneamine with nitropropane, used as solvent.. to give the thermodynamically more stable syn-beta-nitroamine product.

引用

页码：549 / 555

页数：7

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