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P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable P-Tether Systems for the Desymmetrization of C2-Symmetric 1,3-anti-Diols.

ABSTRACT: The development of P-stereogenic bicyclo[4.3.1]phosphite borane tether systems for the desymmetrization of C2-symmetric dienediols is reported. This report highlights preliminary studies including tether installation and removal as well as chemoselective functionalization of the exocyclic olefin via diimide reduction or cross-metathesis. Most notably, a divergent oxidation strategy allows for the transformation of the bicyclic phosphite borane complexes to the corresponding phosphate or thiophosphate systems, highlighting the electronic attenuation of this P-tether system.

SUBMITTER: Markley JL

PROVIDER: S-EPMC5595702 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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P-Stereogenic Bicyclo[4.3.1]phosphite Boranes: Synthesis and Utility of Tunable P-Tether Systems for the Desymmetrization of C<sub>2</sub>-Symmetric 1,3-anti-Diols.

Markley Jana L JL Hanson Paul R PR

Organic letters 20170504 10

The development of P-stereogenic bicyclo[4.3.1]phosphite borane tether systems for the desymmetrization of C<sub>2</sub>-symmetric dienediols is reported. This report highlights preliminary studies including tether installation and removal as well as chemoselective functionalization of the exocyclic olefin via diimide reduction or cross-metathesis. Most notably, a divergent oxidation strategy allows for the transformation of the bicyclic phosphite borane complexes to the corresponding phosphate ...[more]

PMID: 28471175

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