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Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins.

ABSTRACT: Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiated syn-1,2-diols, stereodefined amino-polyols, and syn-pyrans, structures ubiquitous in medicinally important complex molecules found in Nature. We also demonstrate that a C-H oxidation approach to the synthesis of these motifs is orthogonal and complementary to other state-of-the-art methods.

SUBMITTER: Gormisky PE

PROVIDER: S-EPMC3182113 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Synthetic versatility in C-H oxidation: a rapid approach to differentiated diols and pyrans from simple olefins.

Gormisky Paul E PE White M Christina MC

Journal of the American Chemical Society 20110727 32

Conventionally, C-H oxidation reactions are used to install functional groups. The use of C-H oxidation to transform simple starting materials into highly versatile intermediates, which enable rapid access to a range of complex target structures, is a new area with tremendous potential in synthesis. Herein we report a Pd(II)/sulfoxide-catalyzed allylic C-H oxidation to form anti-1,4-dioxan-2-ones from homoallylic oxygenates. These versatile building blocks are rapidly elaborated to differentiate ...[more]

PMID: 21744821

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