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

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Selective Synthesis of C1-Symmetric BINOL-phosphates and P-chiral Phosphoramides Using Directed ortho-Lithiation
Organic Letters ( IF 4.9 ) Pub Date : 2021-08-27 , DOI: 10.1021/acs.orglett.1c02430
Rohan Volpe ₁ , Hanson Y-L Law ₁ , Jonathan M White ₂ , Bernard L Flynn ₁

Affiliation

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.

中文翻译：

使用定向正锂化选择性合成 C1-对称 BINOL-磷酸盐和 P-手性磷酰胺

定向邻位锂化 (DoL) 已被开发为用于邻位取代 BINOL-磷酸和BINOL- N-三氟甲基磷酰胺(BINOL-P-酸)的有效方法。它可用于单取代或双取代的 BINOL-P-酸的快速组装，包括通过迭代 DoL 进行的不对称置换。最重要的是，DoL 已被证明在伪C ₂-对称 BINOL- N-三氟甲基磷酰胺的非对映选择性去对称化中非常有效，提供手性 P 基团。

更新日期：2021-09-17

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