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Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement.

ABSTRACT: Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of ∼23 kcal mol^-1 with isoenergetic favorability (ΔG ∼ 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks.

SUBMITTER: Sobie KM

PROVIDER: S-EPMC8848919 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Construction of vicinal 4°/3°-carbons via reductive Cope rearrangement.

Sobie Kristin M KM Albritton Matthew M Yang Yinuo Y Alves Mariana M MM Roitberg Adrian A Grenning Alexander J AJ

Chemical science 20220121 7

Herein reported is a strategy for constructing vicinal 4°/3° carbons via reductive Cope rearrangement. Substrates have been designed which exhibit Cope rearrangement kinetic barriers of ∼23 kcal mol-1 with isoenergetic favorability (ΔG ∼ 0). These fluxional/shape-shifting molecules can be driven forward by chemoselective reduction to useful polyfunctionalized building blocks. ...[more]

PMID: 35308853

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