Pyruvates are extremely attractive building blocks in organic synthesis due to the high density of reactive centres and double chemical nature (electrophilic and nucleophilic under basic conditions). However, the same double nature sets a narrow pH range for these molecules to engage in productive chemical transformations, which has greatly limited the application of this building block. This work presents a novel pyruvate equivalent (2) resistant to basic conditions. It has been used in the palladium-catalysed enolate arylation reaction, unknown to this class of compounds so far. One-pot addition of electrophiles can further functionalize the pyruvate equivalent to deliver valuable tertiary and quaternary centers at the alpha position (5 and 6). The deprotection of the products shown in Figure 1 to reveal the pyruvic acids or esters is also mild, high yield and can be performed in one-pot. The enolate arylation reaction has been previously used for the de novo building of a variety of heteroaromatic compounds in excellent yields. However, these methodologies could not deliver carbonyl-containing rings, which are widely found in bioactive natural products such as lavendamycin, delavirdine, kynapcin-24 and acromelic acid. More details on how methyl-OBO ketone addresses this problem to be presented at the conference.

OBO-methyl-ketone: A versatile pyruvate equivalent

253rd National Meeting (2017)

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