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A Highly cis-Selective Cascade aza-Michael/Aldol Annulation of Tetrahydroisoquinolines with Ethyl(2-Formylphenyl) Vinylphosphonates to Construct cis-3-Aminomethyl-4-Hydroxyphosphadihydrocoumarins

A Highly cis-Selective Cascade aza-Michael/Aldol Annulation ...

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中国化学会·第十五届全国有机合成化学学术研讨会

作者： Qinghe Wang Huang Tiao 吴明书 College of Chemistry & Chemical Engineering Hainan Normal University 海南师范大学

Coumarins are common structural motifs that are found in a variety of natural products and *** them, 3,4-dihydrocoumarins have shown many biological activities such as anti-cancer, anti-inflammatory actions, anti-microbial properties, anti-tumor, anti-oxidation agents, etc. The organophosphorus compounds often exhibited biochemical activity similar to that of naturally occurring carboxylic acids and their derivatives. Therefore, as phosphorous analogues of dihydrocoumarin, the phosphadihydrocoumarins would have pharmacological activities similar to those described for *** a consequence, we were attracted in developing efficient methods for the construction of a number of phosphadihydrocoumarins, we devised a new synthetic intermediate based on vinylphosphonate and hope to use it as a new synthon for the construction of phosphadihydrocoumarins with the purpose of making focused chemical libraries useful for synthetic methodology research and drug discovery. Here in, we describe a highly cis-selective cascade aza-Michael/Aldol-like annulation of ethyl(2-formylphenyl)vinylphosphonates with tetrahydroisoquinolines for the construction cis-3-aminomethyl-4-hydroxyphosphadihydrocoumarins which could be readily converted into β-hydroxyl-β’-amino alkylphosphonates under simple *** is also worth noting that the direct accessing of 1,3-amino alcohols, which is attracting great attention in recently, was achieved in this process.

关键词： phosphadihydrocoumarin organophosphorus compound dihydrocoumarin

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