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Ligand-Enabled β-C(sp³ )-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant.

ABSTRACT: The development of C(sp³ )-H functionalization reactions that use common protecting groups and practical oxidants remains a significant challenge. Herein we report a monoprotected aminoethyl thioether (MPAThio) ligand-enabled β-C(sp³ )-H lactamization of tosyl-protected aliphatic amides using tert-butyl hydrogen peroxide (TBHP) as the sole oxidant. This protocol features exceedingly mild reaction conditions, reliable scalability, and the use of practical oxidants and protecting groups. Further derivatization of the β-lactam products enables the synthesis of a range of biologically important motifs including β-amino acids, γ-amino alcohols, and azetidines.

SUBMITTER: Zhuang Z

PROVIDER: S-EPMC9439703 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Ligand-Enabled β-C(sp3 )-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant.

Zhuang Zhe Z Liu Shuang S Cheng Jin-Tang JT Yeung Kap-Sun KS Qiao Jennifer X JX Meanwell Nicholas A NA Yu Jin-Quan JQ

Angewandte Chemie (International ed. in English) 20220714 34

The development of C(sp3 )-H functionalization reactions that use common protecting groups and practical oxidants remains a significant challenge. Herein we report a monoprotected aminoethyl thioether (MPAThio) ligand-enabled β-C(sp3 )-H lactamization of tosyl-protected aliphatic amides using tert-butyl hydrogen peroxide (TBHP) as the sole oxidant. This protocol features exceedingly mild reaction conditions, reliable scalability, and the use of practical oxidants and protec ...[more]

PMID: 35790471

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