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Mini-Reviews in Organic Chemistry


ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Recent Developments in Nucleophilic Radical Addition to Imines: the Key Role of Transition Metals and the New Porta Radical-Type Version of the Mannich and Strecker Reactions

Author(s): Nadia Pastori, Cristian Gambarotti and Carlo Punta

Volume 6, Issue 3, 2009

Page: [184 - 195] Pages: 12

DOI: 10.2174/157019309788922702

Price: $65


This review summarizes the interesting results obtained during the last decade in the radical aminoalkylation of a wide range of nucleophilic radicals (deriving from hydrocarbons, ethers, alcohols, halogenated derivatives and amides) promoted by transition metals. We focus on the two main procedures which recently yielded the most relevant results in this field: the dimethylzinc-air process and the new Porta reaction, based on the Ti(III)/hydroperoxide system. These protocols often provide competitive alternatives to classical landmark transformations, like the Mannich reaction and the Strecker synthesis. Moreover, a brief overview of other significant examples is given in the last section of the review.

Keywords: Imine, nucleophilic radical addition, dimethylzinc, titanium trichloride, transition metal, hydroperoxide

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