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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 32(10), p. 6504, 2012

DOI: 10.1039/c2ob25901j

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Reductive hydroxyalkylation/alkylation of amines with lactones/esters

Journal article published in 2012 by Yu-Huang Wang, 黄培强, Jian-Liang Ye, Ai-E. Wang, Pei-Qiang Huang ORCID
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the amides with an excess of DIBAL-H. Different from the reduction of Weinreb amides with DIBAL-H where aldehydes are formed, the reduction of the in situ formed Weinreb amides yielded amines. Moreover, this method is not limited to Weinreb amides, instead, it also works for other amides in general. A plausible mechanism is suggested to account for the outcome of the reactions. ; NSF of China [20902075]; Natural Science Foundation of Fujian Province [2009J05037, 2011J01056]; Specialized Research Fund for the Doctoral Program of Higher Education [20090121120007]; Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education of China