Organocatalyzed solvent-free aza-Henry reaction:: A breakthrough in the one-pot synthesis of 1,2-diamines

被引：68

作者：

Bernardi, L ^{[1
]}

Bonini, BF ^{[1
]}

Capitò, E ^{[1
]}

Dessole, G ^{[1
]}

Comes-Franchini, M ^{[1
]}

Fochi, M ^{[1
]}

Ricci, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, Fac Chim Ind, I-40136 Bologna, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 23期

关键词：

D O I：

10.1021/jo0488762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nitrogen-containing superbase such as TMG was found to be an effective catalyst for the reaction between N-diphenylphosphinoyl imines and nitroalkanes. Exploiting a protocol that avoids the use of any solvent also during workup procedure, we synthesized a series of beta-nitroammes in excellent yields and high diastereomeric ratios. These results, combined with the capability of the indium in conjunction with Zn as the stoichiometric reducing agent to perform in aqueous medium reduction of the nitro group under mild reaction conditions, led us to devise a three-step, one-pot synthesis of a range of 1,2-diamines, making use of environmentally friendly procedures in the various steps.

引用

页码：8168 / 8171

页数：4

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