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Generation of multifunctionalized nucleophilic carbenes

Description: With the aim of developing a method that allows the generation of nucleophilic carbenes at a cryogenic temperature, we focused on an iminium salt derived from β-silyl-α,β-epoxyaldehydes, which can potentially generate a nucleophilic carbene via deprotonation of a proton on an iminium carbon atom, ring-opening of epoxide and Brook rearrangement of the resulting α-silyl alkoxide. We devised a method for the preparation of the substrates and found that some structural modification of the substrates is required to successfully generate a nucleophilc carbene. During the attempt, we also found that 1,n-dipole (n ≠3), a new class of synthons, can serve important intermediates in the synthesis of complex molecules.

Funder: Japan Society for the Promotion of Science

Amount: ¥4,030,000

Funding type: fellowship

Funder scheme: Grant-in-Aid for Young Scientists (B)

Investigator: Michiko SASAKI (lead)

Institution: Hiroshima University

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Funded outputs count: 4

Funder award ID: 22790011