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Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.

ABSTRACT: Despite the rapid growth of enantioselective halolactonization reactions in recent years, most are effective only when forming smaller (6,5,4-membered) rings. Seven-membered ε-lactones, are rarely formed with high selectivity, and never without conformational bias. We describe the first highly enantioselective 7-exo-trig iodolactonizations of conformationally unbiased ε-unsaturated carboxylic acids, effected by an unusual combination of a bifunctional BAM catalyst, I₂, and I(iii) reagent (PhI(OAc)₂:PIDA).

SUBMITTER: Payne JL

PROVIDER: S-EPMC9214890 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Enantioselective iodolactonization to prepare ε-lactone rings using hypervalent iodine.

Payne Jenna L JL Deng Zihang Z Flach Andrew L AL Johnston Jeffrey N JN

Chemical science 20220608 24

Despite the rapid growth of enantioselective halolactonization reactions in recent years, most are effective only when forming smaller (6,5,4-membered) rings. Seven-membered ε-lactones, are rarely formed with high selectivity, and never without conformational bias. We describe the first highly enantioselective 7-<i>exo</i>-trig iodolactonizations of conformationally unbiased ε-unsaturated carboxylic acids, effected by an unusual combination of a bifunctional BAM catalyst, I<sub>2</sub>, and I(ii ...[more]

PMID: 35799806

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