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Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective ?-C(sp3)-H Acetalization.

ABSTRACT: C(sp3)-H bond functionalization has emerged as a robust tool enabling rapid construction of molecular complexity from simple building blocks, and the development of asymmetric versions of this reaction creates a powerful methodology to access enantiopure sp3-rich materials. Herein, we report the stereoselective functionalization of C(sp3)-H bonds of cyclic ethers employing a photochemically active diaryliodonium salt in combination with an anionic phase-transfer catalyst. The synthetic strategy outlined herein allows for regio- and stereochemical control in the ?-C-H acetalization of furans and pyrans using alcohol nucleophiles, thus providing the ability to control the configuration at the stereogenic exocyclic acetal carbon.

SUBMITTER: Ye B

PROVIDER: S-EPMC6448391 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(sp3)-H Acetalization.

Ye Baihua B Zhao Jie J Zhao Ke K McKenna Jeffrey M JM Toste F Dean FD

Journal of the American Chemical Society 20180625 26

C(sp3)-H bond functionalization has emerged as a robust tool enabling rapid construction of molecular complexity from simple building blocks, and the development of asymmetric versions of this reaction creates a powerful methodology to access enantiopure sp3-rich materials. Herein, we report the stereoselective functionalization of C(sp3)-H bonds of cyclic ethers employing a photochemically active diaryliodonium salt in combination with an anionic phase-transfer ...[more]

PMID: 29939024

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