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

doi:10.1021/acs.orglett.1c02430

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

Medicinal Chemistry

Research output: Contribution to journal › Article › Research › peer-review

8 Citations (Scopus)

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 language	English
Pages (from-to)	7055-7058
Number of pages	4
Journal	Organic Letters
Volume	23
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.1c02430
Publication status	Published - 17 Sept 2021

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10.1021/acs.orglett.1c02430

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

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.",

author = "Rohan Volpe and Law, \{Hanson Y.L.\} and White, \{Jonathan M.\} and Flynn, \{Bernard L.\}",

note = "Funding Information: Dedicated to the memory of Professor Victor Snieckus (Aug 1, 1937–Dec 8, 2020). We thank the Australian Research Council for financial support (DP150103131) and Dr. Jamie Simpson for valuable discussions. Publisher Copyright: {\textcopyright}",

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doi = "10.1021/acs.orglett.1c02430",

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T1 - Selective Synthesis of C1-Symmetric BINOL-phosphates and P-chiral Phosphoramides Using Directed ortho-Lithiation

AU - Volpe, Rohan

AU - Law, Hanson Y.L.

AU - White, Jonathan M.

AU - Flynn, Bernard L.

N1 - Funding Information: Dedicated to the memory of Professor Victor Snieckus (Aug 1, 1937–Dec 8, 2020). We thank the Australian Research Council for financial support (DP150103131) and Dr. Jamie Simpson for valuable discussions. Publisher Copyright: ©

PY - 2021/9/17

Y1 - 2021/9/17

N2 - 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.

AB - 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.

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U2 - 10.1021/acs.orglett.1c02430

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

Abstract

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Chiral Catalysts by Rational Design

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

Abstract

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Chiral Catalysts by Rational Design

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