Selective Synthesis of C1-Symmetric BINOL-phosphates and P-chiral Phosphoramides Using Directed ortho-Lithiation

Rohan Volpe, Hanson Y.L. Law, Jonathan M. White, Bernard L. Flynn

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Abstract

Directed ortho-lithiation (DoL) has been developed as an effective method for the ortho-substitution of BINOL-phosphoric acid and BINOL-N-triflylphosphoramide (BINOL-P-acids). It can be employed in the rapid assembly of either mono- or disubstituted BINOL-P-acids, including unsymmetrical disubstitution through iterative DoL. Most significantly, DoL has proven to be highly effective in the diastereoselective desymmetrization of pseudo-C2-symmetric BINOL-N-triflylphosphoramide, affording a chiral P-group.

Original languageEnglish
Pages (from-to)7055-7058
Number of pages4
JournalOrganic Letters
Volume23
Issue number18
DOIs
Publication statusPublished - 17 Sep 2021

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