Abstract
A new method for imine synthesis by way of quinone-catalyzed oxidative deformylation of 1,2-amino alcohols is reported. A wide range of readily accessible amino alcohols and primary amines can be reacted to provide N-protected imine products. The methodology presented provides a novel organocatalytic approach for imine synthesis and demonstrates the synthetic versatility of quinone-catalyzed oxidative C–C bond cleavage.
Highlights
Imines are extremely versatile intermediates in organic chemistry [1-3]
Only a few reports describing the oxidative deformylation of amino alcohols have been published [33-35], and in all of these reports stoichiometric oxidants, such as NaIO4 and Pb(OAc)[4], must be employed to enable the desired transformations
Given that 1,2-amino alcohols are readily accessible from feedstock chemicals such as styrenes [36-38] and amino acids [39], the development of a new methodology to transform these materials into high-value imine products under catalytic conditions has the potential to be broadly useful
Summary
Imines are extremely versatile intermediates in organic chemistry [1-3]. many synthetic methods have been developed for the preparation of imines (Scheme 1). We report a new method that utilizes quinone catalysis to enable the synthesis of imines via oxidative deformylation of amino alcohols. To further exploit the utility of this chemistry, we sought to develop a new method for the preparation of a wide range of imine products through the quinonecatalyzed deformylation of 1,2-amino alcohols.
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