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1-Hydroxy-2-methyl-2-propyl Isocyanide (HMPI) as a New Convertible Isocyanide for the Ugi Four-Component-Coupling Reaction

Masato Oikawa, Yutaro Sugamata, Manami Chiba, Koichi Fukushima, Yuichi Ishikawa

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Abstract

The Ugi reaction is a useful four-component coupling reaction for α-(acylamino)amide. However, selective transformation of the two amides is generally difficult. Here, we report 1-hydroxy-2-methyl-2-propyl isocyanide (HMPI) as a new member of a ‘convertible isocyanide’ class used to solve the problem. HMPI is odorless and shows good reactivity in the Ugi reaction to give N -(1-hydroxy-2-methyl-2-propyl) amides, which are smoothly converted into esters upon Zn(OTf) 2 -mediated solvolysis. Overall, structurally diverse α-amino acid esters are readily accessible in two steps by using HMPI.

About this research paper

What this paper is about

The Ugi reaction is a useful four-component coupling reaction for α-(acylamino)amide. However, selective transformation of the two amides is generally difficult. Here, we report 1-hydroxy-2-methyl-2-propyl isocyanide (HMPI) as a new member of a ‘convertible isocyanide’ class used to solve the problem. HMPI is odorless and shows good reactivity in the Ugi reaction to give N -(1-hydroxy-2-methyl-2-propyl) amides, which are smoothly converted into esters upon Zn(OTf) 2 -mediated solvolysis. Overall, structurally diverse α-amino acid esters are readily accessible in two steps by using HMPI.

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Available abstract

The Ugi reaction is a useful four-component coupling reaction for α-(acylamino)amide. However, selective transformation of the two amides is generally difficult. Here, we report 1-hydroxy-2-methyl-2-propyl isocyanide (HMPI) as a new member of a ‘convertible isocyanide’ class used to solve the problem. HMPI is odorless and shows good reactivity in the Ugi reaction to give N -(1-hydroxy-2-methyl-2-propyl) amides, which are smoothly converted into esters upon Zn(OTf) 2 -mediated solvolysis. Overall, structurally diverse α-amino acid esters are readily accessible in two steps by using HMPI.

Key concepts: Isocyanide, Chemistry, Ugi reaction, Amide, Reactivity (psychology), Solvolysis, Component (thermodynamics), Combinatorial chemistry

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1-Hydroxy-2-methyl-2-propyl Isocyanide (HMPI) as a New Convertible Isocyanide for the Ugi Four-Component-Coupling Reaction — Research Paper | ScholarLens